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194995-47-6

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194995-47-6 Usage

General Description

Propanoic acid, 2-methyl-, 1-[[(4-nitrophenoxy)carbonyl]oxy]ethyl ester is a chemical compound commonly used as a pesticide and herbicide. It is an ester formed from propanoic acid, 2-methyl and 2-(4-nitrophenoxy)ethyl. The compound acts as a selective herbicide that is used to control broadleaf weeds and sedges in various crops, including cereals, rice, and turf. It works by inhibiting the growth of the weed and eventually leading to its death. However, it is important to note that this chemical should be used with caution and in accordance with safety guidelines due to its potential toxicity to humans and the environment.

Check Digit Verification of cas no

The CAS Registry Mumber 194995-47-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,4,9,9 and 5 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 194995-47:
(8*1)+(7*9)+(6*4)+(5*9)+(4*9)+(3*5)+(2*4)+(1*7)=206
206 % 10 = 6
So 194995-47-6 is a valid CAS Registry Number.

194995-47-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-nitrophenoxy)carbonyloxyethyl 2-methylpropanoate

1.2 Other means of identification

Product number -
Other names 1-isobutanoyloxyethyl p-nitrophenyl carbonate

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:194995-47-6 SDS

194995-47-6Synthetic route

(1-chloroethyl)-(4-nitrophenyl)carbonate
101623-69-2

(1-chloroethyl)-(4-nitrophenyl)carbonate

mercuric dimethyl acetate
19348-33-5

mercuric dimethyl acetate

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
With acetic acid Heating;85%
In dichloromethane at 45℃; for 24h;52%
isobutyric Acid
79-31-2

isobutyric Acid

(1-chloroethyl)-(4-nitrophenyl)carbonate
101623-69-2

(1-chloroethyl)-(4-nitrophenyl)carbonate

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: isobutyric Acid With zinc(II) oxide In toluene at 105℃; for 1h;
Stage #2: (1-chloroethyl)-(4-nitrophenyl)carbonate; sodium iodide In toluene at 60℃; for 24h; Product distribution / selectivity;
75%
With sodium iodide; zinc(II) oxide at 60 - 70℃; for 24h;40 mg
4-nitro-phenol
100-02-7

4-nitro-phenol

carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

isobutyric Acid
79-31-2

isobutyric Acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 4-nitro-phenol; carbonochloridic acid 1-chloro-ethyl ester With tributyl-amine In toluene at 20℃;
Stage #2: isobutyric Acid With zinc(II) oxide; sodium iodide In toluene at 75℃; for 10h; Product distribution / selectivity;
60%
4-nitro-phenol
100-02-7

4-nitro-phenol

thiophosphoric acid-chloride O,O'-diisobutyl ester

thiophosphoric acid-chloride O,O'-diisobutyl ester

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / TEA / Ambient temperature
2: 85 percent / MeCO2H / Heating
View Scheme
4-nitro-phenol
100-02-7

4-nitro-phenol

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: pyridine / dichloromethane / 0.17 h / 0 - 4 °C
1.2: 20 °C
2.1: zinc(II) oxide; sodium iodide / 24 h / 60 - 70 °C
View Scheme
H-Gpn-OH
60142-96-3

H-Gpn-OH

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

gabapentin enacarbil
478296-72-9

gabapentin enacarbil

Conditions
ConditionsYield
With chloro-trimethyl-silane; tributyl-amine In toluene at 20℃; for 24h; Product distribution / selectivity;100%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl isobutyrate

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl isobutyrate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 5℃; for 4h;88.2%
(7S)-4,7,8-trimethyl-2-[[1-[[6-(trifluoromethyl)-3-pyridyl]methyl]pyrazol-4-yl]methylamino]-5,7-dihydropteridin-6-one

(7S)-4,7,8-trimethyl-2-[[1-[[6-(trifluoromethyl)-3-pyridyl]methyl]pyrazol-4-yl]methylamino]-5,7-dihydropteridin-6-one

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-((((1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-yl)methyl)((7S)-4,7,8-trimethyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)carbamoyl)oxy)ethyl isobutyrate

1-((((1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-yl)methyl)((7S)-4,7,8-trimethyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)carbamoyl)oxy)ethyl isobutyrate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 100℃; for 24h; Sealed tube;85.16%
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

C17H22ClNO6

C17H22ClNO6

Conditions
ConditionsYield
Stage #1: (R)-(-)-baclofen hydrochloride With chloro-trimethyl-silane; triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: 1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl 2-methylpropanoate In dichloromethane at 20℃; for 3h;
73%
methyl (2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-2-carboxylate

methyl (2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-2-carboxylate

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-(1-(isobutyryloxy)ethyl) 2-methyl (2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-1,2-dicarboxylate

1-(1-(isobutyryloxy)ethyl) 2-methyl (2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;67%
CH2O2*C24H32N2O4S3

CH2O2*C24H32N2O4S3

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

isobutyric acid 1-{1-[2-(benzyloxycarbonylmethylcarbamoyl)-3-phenylpropyldisulfanylmethyl]-3-methanesulfinylpropylcarbamoyloxy}ethyl ester

isobutyric acid 1-{1-[2-(benzyloxycarbonylmethylcarbamoyl)-3-phenylpropyldisulfanylmethyl]-3-methanesulfinylpropylcarbamoyloxy}ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 72h;59%
(2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-2-carboxylic acid

(2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)pyrrolidine-2-carboxylic acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)-1-((1-(isobutyryloxy)ethoxy)carbonyl)pyrrolidine-2-carboxylic acid

(2S,4S)-4-(3-((4-(dimethylamino)-4-phenylcyclohexyl)methyl)phenoxy)-1-((1-(isobutyryloxy)ethoxy)carbonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;47%
C22H28NO6P

C22H28NO6P

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

{4-ethoxy-1-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]-4-oxobutyl}(2-phenylethyl)phosphinic acid

{4-ethoxy-1-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]-4-oxobutyl}(2-phenylethyl)phosphinic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 - 20℃;40%
C32H45N7O3

C32H45N7O3

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

C39H55N7O7

C39H55N7O7

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Inert atmosphere;30.91%
C30H43N7O2

C30H43N7O2

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

C37H53N7O6

C37H53N7O6

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere;30.91%
C2HF3O2*C17H26N2O4S3

C2HF3O2*C17H26N2O4S3

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

isobutyric acid 1-{1-2-[2-(carboxymethylcarbamoyl)-3-phenylpropyldisulfanylmethyl]-3-methanesulfinylpropylcarbamoyloxy}ethyl ester

isobutyric acid 1-{1-2-[2-(carboxymethylcarbamoyl)-3-phenylpropyldisulfanylmethyl]-3-methanesulfinylpropylcarbamoyloxy}ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 21h;28.1%
CL191,121
161855-50-1

CL191,121

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2R,3R)-2-[(1-isobutyryloxy-ethoxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2R,3R)-2-[(1-isobutyryloxy-ethoxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2R,3R)-2-[(1-isobutyryloxy-ethoxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2R,3R)-2-[(1-isobutyryloxy-ethoxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 77 percent / K2CO3 / acetonitrile / Ambient temperature
View Scheme
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

pregabilin
148553-50-8

pregabilin

A

3-{[(α-(R)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid
1174748-30-1

3-{[(α-(R)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid

B

3-{[(α-(S)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid

3-{[(α-(S)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-5-(S)-methylhexanoic acid

Conditions
ConditionsYield
Stage #1: pregabilin With chloro-trimethyl-silane; triethylamine In dichloromethane at 0℃; for 0.25h;
Stage #2: 1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl 2-methylpropanoate In dichloromethane at 20℃; for 1.5h;
1-{(4-bromophenylalaninyl)aminomethyl}-1-cyclohexane-acetic acid
478296-99-0

1-{(4-bromophenylalaninyl)aminomethyl}-1-cyclohexane-acetic acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-{[N-[(α-isobutanoyloxyethoxy)carbonyl]-4-bromophenylalaninyl]-aminomethyl}-1-cyclohexaneacetic acid
478296-98-9

1-{[N-[(α-isobutanoyloxyethoxy)carbonyl]-4-bromophenylalaninyl]-aminomethyl}-1-cyclohexaneacetic acid

Conditions
ConditionsYield
Stage #1: 1-{(4-bromophenylalaninyl)aminomethyl}-1-cyclohexane-acetic acid With chloro-trimethyl-silane; triethylamine In dichloromethane at 0℃; for 0.25h;
Stage #2: 1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl 2-methylpropanoate In dichloromethane at 0 - 20℃; for 7h;
(5-tert-butyl-2-oxo-1,3-dioxol-4-yl)methyl (2S)-2-[(3S)-3-aminopyrrolidin-1-yl]-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)propanoate trihydrochloride

(5-tert-butyl-2-oxo-1,3-dioxol-4-yl)methyl (2S)-2-[(3S)-3-aminopyrrolidin-1-yl]-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)propanoate trihydrochloride

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(5-tert-butyl-2-oxo-1,3-dioxol-4-yl)methyl (2S)-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)-2-{(3S)-3-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pyrrolidin-1-yl}propanoate
1277173-49-5

(5-tert-butyl-2-oxo-1,3-dioxol-4-yl)methyl (2S)-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)-2-{(3S)-3-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pyrrolidin-1-yl}propanoate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 11h; Cooling with ice;
(2S)-2-[(3S)-3-aminopyrrolidin-1-yl]-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)propanoic acid
1277173-20-2

(2S)-2-[(3S)-3-aminopyrrolidin-1-yl]-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)propanoic acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(2S)-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)-2-{(3S)-3-[({1[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pyrrolidin-1-yl}propanoic acid
1277173-19-9

(2S)-3-(4,5-dihydroimidazo[1,5-a]quinolin-3-yl)-2-{(3S)-3-[({1[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pyrrolidin-1-yl}propanoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;
(2S)-5-amino-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoic acid
1224846-59-6

(2S)-5-amino-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoic acid

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(2S)-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)-5-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pentanoic acid
1224847-42-0

(2S)-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)-5-[({1-[(2-methylpropanoyl)oxy]ethoxy}carbonyl)amino]pentanoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 15h;
C29H32ClFN2O4

C29H32ClFN2O4

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

C36H42ClFN2O8

C36H42ClFN2O8

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20 - 25℃; Inert atmosphere;555 mg
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; Inert atmosphere;555 mg
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride salt

1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride salt

(E)-1-(((amino(4-(((5-((3-ethoxy-3-oxopropyl)(pyridin-2-yl)carbamoyl)-1-methyl-1H-benzo[d]imidazol-2-yl)methyl)amino)phenyl)methylene)carbamoyl)oxy)ethyl isobutyrate

(E)-1-(((amino(4-(((5-((3-ethoxy-3-oxopropyl)(pyridin-2-yl)carbamoyl)-1-methyl-1H-benzo[d]imidazol-2-yl)methyl)amino)phenyl)methylene)carbamoyl)oxy)ethyl isobutyrate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 48h;0.15 g
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(2S)-5-({[(1R)-1-(isobutyryloxy)ethoxy]carbonyl}amino)-2-{[1-(trans-4-methylcyclohexyl)-1H-imidazol-4-yl]methyl}valeric acid
1335138-79-8

(2S)-5-({[(1R)-1-(isobutyryloxy)ethoxy]carbonyl}amino)-2-{[1-(trans-4-methylcyclohexyl)-1H-imidazol-4-yl]methyl}valeric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / -5 - 0 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRALCEL OJ-H / hexane; isopropyl alcohol / Resolution of racemate
3: triethylamine; sodium hydroxide / acetonitrile; water / 20 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRAZYME L-2,C4 / aq. phosphate buffer; tert-butyl methyl ether / 38 h / 20 °C / Enzymatic reaction
3: triethylamine; sodium hydroxide / acetonitrile; water / 20 h / 0 °C
View Scheme
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

(2S)-5-({[(1S)-1-(isobutyryloxy)ethoxy]carbonyl}amino)2-{[1-(trans-4-methylcyclohexyl)-1H-imidazol-4-yl]methyl}valeric acid

(2S)-5-({[(1S)-1-(isobutyryloxy)ethoxy]carbonyl}amino)2-{[1-(trans-4-methylcyclohexyl)-1H-imidazol-4-yl]methyl}valeric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRALCEL OJ-H / hexane; isopropyl alcohol / Resolution of racemate
3: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 0 °C
View Scheme
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl (R)-isobutyrate

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl (R)-isobutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRALCEL OJ-H / hexane; isopropyl alcohol / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRAZYME L-2,C4 / aq. phosphate buffer; tert-butyl methyl ether / 38 h / 20 °C / Enzymatic reaction
View Scheme
1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester
194995-47-6

1-[[(4-nitrophenoxy)carbonyl]oxy]-2-methylpropionic acid ethyl ester

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl (S)-isobutyrate

1-{[(1,1,1,3,3,3-hexafluoro-2-propoxy)carbonyl]oxy}ethyl (S)-isobutyrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 4 h / 0 - 5 °C
2: CHIRALCEL OJ-H / hexane; isopropyl alcohol / Resolution of racemate
View Scheme

194995-47-6Relevant articles and documents

PRODRUGS OF KALLIKREIN INHIBITORS

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Page/Page column 127; 138, (2018/05/24)

Disclosed are compounds of formula I, II, and III, and pharmaceutically acceptable salts thereof, which are inhibitors of kallikrein. Also provided are pharmaceutical compositions comprising such a compound, and methods involving use of the compounds and compositions in the treatment and prevention of acquired or hereditary angioedema, or other diseases and conditions characterized by aberrant kallikrein activity. (I) (II) (III)

PROCESSES FOR THE PREPARATION AND PURIFICATION OF GABAPENTIN ENACARBIL

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Page/Page column 26-27, (2010/06/17)

Gabapentin enacarbil was prepared and purified from intermediates such as 1- haloalkyl carbamate or carbonate and diacid acetal skeleton. For example, a 1-haloalkyl carbonate or carbamate was prepared by combining a C1 to C 10 alcohol or C1 to C10 primary amine, a solvent selected from the group consisting of: acetonitrile, C3 to C7 ketone, C5 to C 10 ether, C2 to C7 ester, C5 to C 10 hydrocarbon and a combination thereof; a 1-haloalkyl halo formate of the following formula:(I) wherein each X is independently selected from Br, I, or Cl; R1 is alkyl or H; and a C6 to C21 tertiary amine.

Mono and bis double ester prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

Lin, Yang-I.,Bitha, Panayota,Li, Zhong,Sakya, Subas M.,Strohmeyer, Timothy W.,Lang Jr., Stanley A.,Yang, Youjun,Bhachech, Niraja,Weiss, William J.,Petersen, Peter J.,Jacobus, Nilda V.,Bush, Karen,Testa, Raymond T.

, p. 1811 - 1816 (2007/10/03)

Mono and bis double ester prodrugs of aminomethyl THF 1β-methylcarbapenems 1 were Mono double ester derivatives (2, 4 and 7) did not demonstrate significantly improved oral activity due to the presence of the charged species. However, bis double ester derivatives (3 and 5) demonstrated enhanced oral activity.

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