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2577-90-4

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2577-90-4 Usage

Definition

ChEBI: An alpha-amino acid ester that is the methyl ester of L-phenylalanine.

Check Digit Verification of cas no

The CAS Registry Mumber 2577-90-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,7 and 7 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2577-90:
(6*2)+(5*5)+(4*7)+(3*7)+(2*9)+(1*0)=104
104 % 10 = 4
So 2577-90-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h2-6,9H,7,11H2,1H3;1H/t9-;/m0./s1

2577-90-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl L-phenylalaninate

1.2 Other means of identification

Product number -
Other names (S)-Methyl 2-amino-3-phenylpropanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2577-90-4 SDS

2577-90-4Synthetic route

methanol
67-56-1

methanol

L-phenylalanine
63-91-2

L-phenylalanine

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With thionyl chloride100%
With thionyl chloride at -10 - 20℃; Inert atmosphere;100%
With thionyl chloride at 0 - 20℃;99%
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate
129397-81-5

methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate

phenylmethanethiol
100-53-8

phenylmethanethiol

A

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

B

9-benzylthiomethylfluorene

9-benzylthiomethylfluorene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide for 0.0333333h; Product distribution; other protected peptides, other thiol, var. TBAF conc., var. time, var. solvent, with or without ultrasound mixing;A n/a
B 100%
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide for 0.05h;A n/a
B 100%
(E)-α-(N-acylamino)cinnamic acid methyl ester
64590-81-4

(E)-α-(N-acylamino)cinnamic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogen; (S)Fc-α-S(C5H5)Fe(C5H3(PPh2)CH(OH)C6H4(PPh2)); [Rh(norbornadiene)2]BF4 In methanol at 25℃; under 750.075 Torr; for 1h; Product distribution / selectivity;100%
With hydrogen; (S)-1-diphenylphosphino-2-[α-(S)-methoxy(o-diphenylphosphinophenyl)methyl]ferrocene; [Rh(norbornadiene)2]BF4 In methanol at 25℃; under 750.075 Torr; for 1h; Product distribution / selectivity;100%
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With Amberlyst A21 In dichloromethane at 0 - 20℃; for 2h; stereoselective reaction;99%
With Amberlyst A21 resin In dichloromethane at 0 - 20℃; for 2h; Reagent/catalyst;99%
With potassium carbonate In dichloromethane; water at 20℃;97%
N-carbobenzoxy-L-phenylalanine methyl ester
35909-92-3

N-carbobenzoxy-L-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogen In methanol at 27℃; under 750.075 Torr; for 2h; Reagent/catalyst; Green chemistry;99%
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate
129397-81-5

methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With piperazine; diethyl {[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]methylidene}propanedioate In ethanol at 20℃; for 0.5h;98%
With sodium azide In N,N-dimethyl-formamide at 50℃; for 3h;97%
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 25℃; Green chemistry;82%
With aluminium trichloride; N,N-dimethyl-aniline In dichloromethane for 4h; Heating;
With Octanethiol; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
N-Cbz-L-Asp
1152-61-0

N-Cbz-L-Asp

A

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

B

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester
33605-72-0

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
In N-methyl-acetamide; waterA 95.5%
B n/a
Phenylalanine
150-30-1

Phenylalanine

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In methanol; water94.5%
N-(((tert-butyldimethylsilyl)oxy)carbonyl)phenylalanine methyl ester
107897-41-6

N-(((tert-butyldimethylsilyl)oxy)carbonyl)phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Ambient temperature;93%
(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-3-phenyl-propionic acid methyl ester
211567-40-7

(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-3-phenyl-propionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
Bio-Rad AG 50W-X2 In ethanol at 45℃; for 1.5h;93%
(S)-2-{3-[2-(3,4-Dihydroxy-phenyl)-ethyl]-ureido}-3-phenyl-propionic acid methyl ester

(S)-2-{3-[2-(3,4-Dihydroxy-phenyl)-ethyl]-ureido}-3-phenyl-propionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With mushroom tyrosinase E.C. 1.14.18.1; oxygen In phosphate buffer; acetonitrile at 20℃;93%
N-Tsoc-phenylalanine methyl ester
228704-07-2

N-Tsoc-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃;92%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.166667h; Inert atmosphere; Schlenk technique;89%
(S)-2-[4-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyloxy)-but-2-ynyloxycarbonylamino]-3-phenyl-propionic acid methyl ester

(S)-2-[4-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyloxy)-but-2-ynyloxycarbonylamino]-3-phenyl-propionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With Amberlite IRA-400 bound triethylammonium tetrathiomolybdate In methanol at 28℃; for 1h; ultrasonication;92%
(S)-methyl-(N-allyloxycarbonyl)phenylalaninate
128369-71-1

(S)-methyl-(N-allyloxycarbonyl)phenylalaninate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran91%
1H,1H,2H,2H-Perfluorodecanethiol
34143-74-3

1H,1H,2H,2H-Perfluorodecanethiol

(S)-methyl 2-(2-nitrophenylsulfonamido)-3-phenylpropanoate
203873-67-0

(S)-methyl 2-(2-nitrophenylsulfonamido)-3-phenylpropanoate

A

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

B

1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;A 91%
B n/a
(S)-methyl 2-(4,5-dimethoxy-2-methylbenzylamino)-3-phenylpropanoate
1363553-45-0

(S)-methyl 2-(4,5-dimethoxy-2-methylbenzylamino)-3-phenylpropanoate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; water In acetonitrile at 20℃; for 48h; Inert atmosphere;91%
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester
51987-73-6

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With phosphoric acid In dichloromethane at 20℃; for 3h;90%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 80 - 82℃; for 3h;70%
With molecular sieve; boron trifluoride diethyl etherate In dichloromethane for 20h; Ambient temperature;
diethyl {[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]methylidene}propanedioate
1222062-82-9

diethyl {[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]methylidene}propanedioate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 2.3h;90%
2-(4-methoxybenzylamino)-3-phenypropionic acid methyl ester
344765-03-3

2-(4-methoxybenzylamino)-3-phenypropionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogenchloride; riboflavin tetraacetate; water In acetonitrile for 1h; pH=3; Irradiation; In air;90%
(S)-2-[3-(4-Hydroxy-phenyl)-ureido]-3-phenyl-propionic acid methyl ester

(S)-2-[3-(4-Hydroxy-phenyl)-ureido]-3-phenyl-propionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With mushroom tyrosinase E.C. 1.14.18.1; oxygen In phosphate buffer; acetonitrile at 20℃;87%
(S)-2-azido-3-phenylpropionic acid methyl ester
116911-32-1

(S)-2-azido-3-phenylpropionic acid methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 12h;85%
With hydrogen; palladium on activated charcoal
L-phenylalanine
63-91-2

L-phenylalanine

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With sulfuric acid In methanol83.2%
With sulfuric acid In methanol
Multi-step reaction with 2 steps
1.1: acetyl chloride / 0.17 h / 10 °C
1.2: 8 h / 10 - 20 °C
2.1: sodium hydroxide / chloroform
View Scheme
N-formyl-L-phenylalanine-methylester
2311-21-9

N-formyl-L-phenylalanine-methylester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol80%
methanol
67-56-1

methanol

N-(1-Benzotriazolylcarbonyl)-L-phenylalanin
81917-69-3

N-(1-Benzotriazolylcarbonyl)-L-phenylalanin

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With TEA at 20℃; for 4h;78%
N,N-bis-allyl-L-phenylalanine methyl ester
79561-72-1

N,N-bis-allyl-L-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With Wilkinson's catalyst In water; acetonitrile for 2h; Heating;76%
(2R,5S)-2-Benzyl-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine
87900-19-4

(2R,5S)-2-Benzyl-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine

A

L-Valine methyl ester
4070-48-8

L-Valine methyl ester

B

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

C

D-phenylalanine methyl ester
21685-51-8

D-phenylalanine methyl ester

Conditions
ConditionsYield
With hydrogenchloride for 10h; Ambient temperature;A n/a
B n/a
C 73%
methyl (2-methoxybenzoyl)phenylalaninate

methyl (2-methoxybenzoyl)phenylalaninate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: methyl (2-methoxybenzoyl)phenylalaninate With Schwartz's reagent In tetrahydrofuran at -5 - 0℃; for 2h; Inert atmosphere;
Stage #2: With ammonium chloride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
68%
methyl N-{[2-(trimethylsilyl)ethyl]sulfonyl}-L-phenylalaninate
106018-94-4

methyl N-{[2-(trimethylsilyl)ethyl]sulfonyl}-L-phenylalaninate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Conditions
ConditionsYield
With hydrogen fluoride; methoxybenzene In dichloromethane at 0℃; for 1h; desulfonylation;65%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate
13122-89-9

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In various solvent(s) at 65℃; for 3h;100%
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane98%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In Dichlorodifluoromethane; water at 20℃; for 3h;96%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; diborane In tetrahydrofuran at 20℃; for 1h;100%
With hydrogen In ethanol at 110℃; under 30003 Torr; Reagent/catalyst; Autoclave; chemoselective reaction;91.1%
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;86%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-Cbz-L-Asp
1152-61-0

N-Cbz-L-Asp

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester
33605-72-0

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
thermolysin-immobilized capsule membrane In chloroform at 45℃; for 24h;100%
thermolysin-immobilized capsule membrane In chloroform at 45℃; for 24h; Mechanism; KM, kcat; other catalyst, rection time, temperature;100%
at 55℃; cross-linked enzyme crystal (T-CLEC);95%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 48h; α-chymotrypsin;100%
With sodium hydroxide In water; ethyl acetate pH=9 - 10;93%
at 25℃; for 0.833333h; enzyme alcalase from Bacillus licheniforms; pH 8.2;
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

acetic anhydride
108-24-7

acetic anhydride

(S)-N-acetylphenylalanine
3618-96-0

(S)-N-acetylphenylalanine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;100%
With sodium hydrogencarbonate In dichloromethane; water at 25℃; for 4h; Schotten-Baumann Reaction;100%
With triethylamine In dichloromethane at 20℃; for 1h;94%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester
51987-73-6

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine100%
copper(II) bis(tetrafluoroborate) at 30 - 35℃; for 0.166667h;99%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; for 1h;99%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

1-boraadamantane-tetrahydrofurane

1-boraadamantane-tetrahydrofurane

1-boraadamantane-L-phenylalanine methyl ester

1-boraadamantane-L-phenylalanine methyl ester

Conditions
ConditionsYield
In dichloromethane100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

methyl (S)-2-[bis(tert-butoxycarbonyl) amino]-3-phenylpropanoate
154409-62-8

methyl (S)-2-[bis(tert-butoxycarbonyl) amino]-3-phenylpropanoate

Conditions
ConditionsYield
With dmap100%
Stage #1: di-tert-butyl dicarbonate; methyl (2S)-2-amino-3-phenylpropanoate With sodium carbonate In tetrahydrofuran; water at 0 - 20℃;
Stage #2: With dmap In acetonitrile at 20℃;
92%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-Boc-D-serine(Bzl)-OH
47173-80-8

N-Boc-D-serine(Bzl)-OH

(S)-2-((R)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-3-phenyl-propionic acid methyl ester
192723-29-8

(S)-2-((R)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane
1-boraadamantane tetrahydrofuranate
61357-36-6

1-boraadamantane tetrahydrofuranate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

C19H28BNO2

C19H28BNO2

Conditions
ConditionsYield
100%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-(tert-butoxycarbonyl)-L-tert-leucine
112695-98-4, 79777-82-5

N-(tert-butoxycarbonyl)-L-tert-leucine

Boc-Ala(tBu)-Phe-OMe

Boc-Ala(tBu)-Phe-OMe

Conditions
ConditionsYield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane100%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

C24H31N3O5

C24H31N3O5

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate
13122-89-9

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate

Conditions
ConditionsYield
With zinc diacetate; sodium acetate In tetrahydrofuran at 60℃; for 24h; Reagent/catalyst; Temperature;100%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-L-Phe-L-Phe-OMe

Fmoc-L-Phe-L-Phe-OMe

Conditions
ConditionsYield
Stage #1: N-Fmoc L-Phe With N,N'-dimethylbenzylamine; isopropyl chloroformate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; acetonitrile at 60℃; for 0.00139167h; Flow reactor;
Stage #2: methyl (2S)-2-amino-3-phenylpropanoate With 1-methyl-1H-imidazole; hydrogenchloride In 1,4-dioxane; water; acetonitrile at 60℃; for 0.0333333h; Flow reactor;
100%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

methyl N-cyclopropylcarbonylphenylalaninate

methyl N-cyclopropylcarbonylphenylalaninate

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 0.0222222h; Flow reactor;99.9%
In diethyl ether for 3h; Heating;57%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

methoxycarbonylmethylamine
616-34-2

methoxycarbonylmethylamine

(S)-PheGly
721-90-4

(S)-PheGly

Conditions
ConditionsYield
Stage #1: methyl (2S)-2-amino-3-phenylpropanoate at 50℃; Ionic liquid; Inert atmosphere;
Stage #2: With trifluoroacetic acid
Stage #3: methoxycarbonylmethylamine Temperature; Further stages;
99.9%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester
15136-32-0, 87976-66-7, 120342-25-8, 5874-73-7

(N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;99%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;99%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;99%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

benzotriazol-1-yl p-aminobenzoate
88744-38-1

benzotriazol-1-yl p-aminobenzoate

L-phenylalanine-N-(4-aminobenzoyl) methyl ester

L-phenylalanine-N-(4-aminobenzoyl) methyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;99%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

benzyl bromide
100-39-0

benzyl bromide

N,N-dibenzyl-L-phenylalanine methyl ester
184774-09-2

N,N-dibenzyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; dimethyl sulfoxide for 12h; Reflux;99%
With sodium hydrogencarbonate In tetrahydrofuran; dimethyl sulfoxide at 85℃; for 16h;
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine
37553-65-4, 64263-83-8, 85466-66-6

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine

Boc-D-Phe(N-Me)-Phe-OMe
934715-26-1

Boc-D-Phe(N-Me)-Phe-OMe

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;99%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;97%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;90%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

t-Boc-D-phenylalanyl-L-phenylalanine methyl ester
94202-58-1

t-Boc-D-phenylalanyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;99%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;98%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride95%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
66863-43-2

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

(S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
900865-72-7

(S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Conditions
ConditionsYield
Stage #1: (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid With benzotriazol-1-ol In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: methyl (2S)-2-amino-3-phenylpropanoate With 4-methyl-morpholine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;
99%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;98%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine
173775-54-7

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine

C24H28FN3O7

C24H28FN3O7

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 25℃; for 12h;99%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(p-toluenesulfonyl)-L-phenylalanine methyl ester
51220-86-1, 149703-21-9, 42384-33-8

N-(p-toluenesulfonyl)-L-phenylalanine methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;99%
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;94%
β‐cyclodextrin In various solvent(s) at 20℃; for 0.75h; pH=8;90%
With erbium(III) triflate In 2-methyltetrahydrofuran for 2h; Green chemistry;
C35H39N3O5
1134603-24-9

C35H39N3O5

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

C45H52N4O7
1134603-27-2

C45H52N4O7

Conditions
ConditionsYield
at 120℃; for 10h; Inert atmosphere; Neat (no solvent); stereoselective reaction;99%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

1-acetyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium tetraphenylborate
1363906-80-2

1-acetyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium tetraphenylborate

(S)-N-acetylphenylalanine
3618-96-0

(S)-N-acetylphenylalanine

Conditions
ConditionsYield
In acetonitrile at 80℃; for 1h; Inert atmosphere;99%

2577-90-4Relevant articles and documents

Propargyloxycarbonyl and propargyl groups for novel protection of amino, hydroxy, and carboxy functions

Kukase,Fukase,Kusumoto

, p. 1169 - 1170 (1999)

The propargyloxycarbonyl group readily introduced to both amino and hydroxy groups by using propargyl chloroformate is stable to neat TFA but is readily cleaved at ambient temperature by treatment with Co2(CO)8 and TFA in CH2Cl2 via formation of an alkyne-Co complex. The propargyl ester similarly serves as a good protecting group for carboxy functions.

Formation of lanthanide complexes with bipyridine-functionalized amide compounds and their unusually high amide reactivity

Araki,Kawaguchi,Kajikawa,Kaneko,Koshimizu

, p. 2729 - 2736 (1999)

The amide of 6-benzoylamino-6'-L-phenylalanyl-amino-2,2'-bipyridine (1a) was efficiently cleaved at 30°C to generate L-phenylalanine ester in methanol almost quantitatively. The reaction followed the Michaelis-Menten type via the 1:1 1a-Ln3+ complex. The half-life time of the scissile amide bond of the complex was as short as 2 min for the complex. The reactions depended on the structure of the substrates, which require 2,2'-bipyridine with two acylamino side chains at the 6,6'-positions and an amino group at the α-position of the scissile carbonyl. The less reactive 6-6'bis(benzoylamino)-2,2'-bipyridine with lanthanide cations formed 1:1 complexes. The formation constants were on the order of 103-105 cu dm/mole in methanol at 30°C. Coordination of the bipyridine nitrogens and the carbonyl oxygens was demonstrated in chloroform although coordination of the carbonyl oxygens was not seen in methanol.

Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations

Capraro, Maria Grazia,Franchi, Paola,Lanzalunga, Osvaldo,Lapi, Andrea,Lucarini, Marco

, p. 6435 - 6443 (2014)

Chiral N-hydroxybenzamides (1H-3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1?-3?. The latter species have been generated by oxidation of 1H-3H with Pb(OAc)4 or hydrogen abstraction from 1H-3H by the tert-butoxyl radical and characterized by UV-vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1?-3? from three chiral benzylic substrates (1-phenylethylamine, 1-phenylethanol, and α-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 ≥ kH(S)/kH(R) ≥ 2.

Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor

?tv?s, Sándor B.,Buchholcz, Balázs,Darvas, Ferenc,Kappe, C. Oliver,Novák, Zoltán,Sipos, Gellért,Wernik, Michaela

supporting information, p. 5625 - 5632 (2021/08/16)

Despite the fact that continuous flow processing exhibits well-established technical advances, aqueous micellar chemistry, a field that has proven extremely useful in shifting organic synthesis to sustainable water-based media, has mostly been explored under conventional batch-based conditions. This is particularly because of the fact that the reliable handling of slurries and suspensions in flow has been considered as a significant technical challenge. Herein, we demonstrate that the strategic application of an oscillatory plug flow reactor enables heterogeneous catalytic reductive aminations in aqueous micellar media enhancing mass transport and facilitating process simplicity, stability and scalability. The micellar flow process enabled a broad range of substrates, including amino acid derivatives, to be successfully transformed under reasonably mild conditions utilizing only very low amounts of Pd/C as a readily available heterogeneous catalyst. The preparative capabilities of the process along with the recyclability of the heterogenous catalyst and the aqueous reaction media were also demonstrated. This journal is

A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters

Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther

supporting information, p. 2099 - 2102 (2021/07/22)

A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of α-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl]2. Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.

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