2018-61-3

Basic information

• Product Name: N-Acetyl-L-phenylalanine
• Synonyms: N-Ac-Phenylalanine;(2S)-2-Acetamido-3-phenylpropanoic acid;(2S)-2-(Acetylamino)-3-phenylpropanoic acid;(2S)-2-(Acetylamino)-3-phenylpropionic acid;(S)-α-(Acetylamino)benzenepropanoic acid;(αS)-α-(Acetylamino)benzenepropanoic acid;H-Ac-Phe-OH;N-propionyl leucine
• CAS NO: 2018-61-3
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• EINECS: 217-959-8
• Product Categories: Phenylalanine [Phe, F];Amino Acids and Derivatives;Ac-Amino Acids;Amino Acids (N-Protected);Biochemistry;N-Acetyl-Amino acid series;Amino Acid Derivatives;Peptide Synthesis;Phenylalanine;Amino Acids Derivatives;chiral;Amino Acid Derivatives;Amino Acids
• Mol File: 2018-61-3.mol
• Article Data: 281

Chemical Properties

• Melting Point: 171-173 °C(lit.)
• Boiling Point: 346.25°C (rough estimate)
• Flash Point: 228.3 °C
• Appearance: White to off-white/Fine Crystalline Powder or Needles
• Density: 1.1878 (rough estimate)
• Vapor Pressure: 4.96E-09mmHg at 25°C
• Refractive Index: 40 ° (C=5, MeOH)
• Storage Temp.: -20°C
• Solubility: Solubility in methanol (almost transparency). Soluble in acetone
• PKA: 3.56±0.10(Predicted)
• CAS DataBase Reference: N-Acetyl-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-phenylalanine(2018-61-3)
• EPA Substance Registry System: N-Acetyl-L-phenylalanine(2018-61-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2018-61-3(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white fine cryst. powder or needles

Uses

It is an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of aspartame. It is applied as an antidepressant.

Uses

N-Acetyl-L-phenylalanine is an protected analogue of L-Phenylalanine (P319415), an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of Aspartame.

Definition

ChEBI: The N-acetyl derivative of L-phenylalanine.

General Description

N-Acetyl-L-phenylalanine is an acetyl analog of L-phenylalanine. It is widely used as a reactant to synthesize methyl or ethyl esters of N-acetyl-L-phenylalanine, which are employed as versatile building blocks in peptide synthesis.

Purification Methods

N-Acetyl-L-phenylalanine is recrystallised from H2O, 20% MeOH/H2O, or CHCl3; dry and store it at 4o. The (DL)-isomer crystallises from H2O, Me2CO, EtOAc, or CHCl3 with m 152-154o and the solubilities in w% at 25o are 0.73 (H2O), 4.3 (Me2CO), 0.79 (EtOAc) and 0.34 (CHCl3) [Kerr & Niemann J Org Chem 23 893 1958, Overby & Ingersoll J Am Chem Soc 73 3363 1951, L: Fu et al. J Am Chem Soc 76 6057 1954, Bender & Glasson J Am Chem Soc 81 1591 1959]. [Beilstein 14 I 238, 4 IV 1575.]

InChI:InChI=1/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/p-1/t10-/m0/s1

Synthetic route

N-acetamido cinnamic acid (55065-02-6, 64590-80-3, 5469-45-4) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane In tetrahydrofuran at 20℃; under 750.075 Torr; for 24h;	100%
With hydrogen; (1+)*BF4(1-) In ethanol; benzene under 20 Torr;	99%
With hydrogen; Rh(nbd)(1)BF4 In dichloromethane at 50℃; under 38787.1 Torr; for 12h;	99%

N-acetyl dehydrophenylalanine methyl ester (52386-78-4) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 22℃; under 38000 Torr;	100%

ethyl N-acetyl-(L)-phenylalaninate (2361-96-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With ammonium bicarbonate; water In dichloromethane for 12h; α-chymotrypsin;	100%
With caesium carbonate In methanol; water for 24h;	99%
With caesium carbonate In methanol; water for 24h; Product distribution; other alcohols;	99%
With α-chymotrypsin In water at 25℃; Rate constant; pH 7.0-7.8;
With bis-Tris propane buffer; calcium chloride at 25℃; Rate constant;

L-phenylalanine (63-91-2) + acetic anhydride (108-24-7) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
In water for 0.0666667h; Irradiation;	98%
With sodium hydroxide In water pH=10; Cooling with ice;	93%
With sodium hydroxide In water at 20℃; for 3h; pH=8; Concentration;	93%

(S)-N-acetylphenylalanine (3618-96-0) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With magnesium iodide In tetrahydrofuran at 120℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube; chemoselective reaction;	98%
With sodium carbonate In methanol; water for 4h;	88%
With sodium carbonate In methanol; water for 4h; Product distribution; other alkali carbonates;	88%
With water In N,N-dimethyl-formamide carbonate buffer (pH=10.5); α-chymotrypsin-cat. hydrolysis (spec. activity);

L-phenylalanine (63-91-2) + acetyl chloride (75-36-5) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;	97%
With pyridine at 20℃;	84.6%

Rh(COD)2 BF4 + N-acetamido cinnamic acid (55065-02-6, 64590-80-3, 5469-45-4) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogen In tetrahydrofuran	97%

(Z)-2-acetamidocinnamic acid + pyrographite (7440-44-0) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogen In methanol; benzene	96.2%

N-acetylphenylalanine methyl ester (21156-62-7, 3618-96-0, 62436-70-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With sodium hydroxide In water Alcalase, pH 7.5;	93.7%
With cross-linked yeast cells (Saccharomyces cerevisiae); water In dimethyl sulfoxide at 30℃; for 48h;

N-acetylphenylalanine methyl ester (21156-62-7, 3618-96-0, 62436-70-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (R)-N-acetylphenylalanine methyl ester (21156-62-7)

Conditions	Yield
With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4 In tetrahydrofuran Ambient temperature;	A 86% B 93%
Yield given. Yields of byproduct given;
With Lecitase Ultra; water; calcium chloride at 30℃; for 12h; pH=8.5; aq. buffer; Enzymatic reaction; enantioselective reaction;

L-phenylalanine (63-91-2) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogenchloride; acetic anhydride In sodium hydrogencarbonate; ethyl acetate	90.3%
With hydrogenchloride; acetic anhydride; triethylamine In water
Multi-step reaction with 2 steps 1: dichloromethane / 16 h / 20 °C 2: dichloromethane / 16.5 h / -40 - 20 °C View Scheme

2-(N-acetylamino)cinnamic acid (55065-02-6, 64590-80-3, 5469-45-4) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole; hydrogen In methanol at 20℃; under 5171.62 Torr; for 24h; Autoclave; enantioselective reaction;	90%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C48H42Fe2O2; hydrogen In methanol at 20℃; under 7600.51 Torr; for 24h; optical yield given as %ee;	88%
With hydrogen In ethanol Product distribution; Ambient temperature; various catalysts;

(S)-N-acetylphenylalanine tert-butyl ester (68277-06-5) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 6h;	90%

L-phenylalanine (63-91-2) + thioacetic acid (507-09-5) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h;	90%

N-acetamido cinnamic acid (55065-02-6, 64590-80-3, 5469-45-4) → (R)-N-acetylphenylalanin (10172-89-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With [Rh(cod)(Xylophos)](1+)*BF4(1-); hydrogen In methanol at 19.85℃; under 760 Torr; for 6h;	A 11% B 89%
With hydrogen; (1+); Dowex HCR-S In methanol; water at 50℃; under 15001.2 Torr; Product distribution; other rhodium(I)-complexes, various reaction conditions: time, pressure and temperatures; other derivatives of acetamidoacryl acid;
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; optically active phosphine In methanol at 20 - 30℃; under 825.07 Torr; for 72h; Product distribution; various di- and triphosphines, other temperatures and times;

alpha-acetaminocinnamic acid (103989-08-8, 104787-34-0) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
	82%

L-phenylalanine (63-91-2) + acetic acid (64-19-7) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 120℃; for 0.333333h; Green chemistry;	73%

L-lysine n-butyl ester (2885-12-3) + ethyl N-acetyl-(L)-phenylalaninate (2361-96-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid butyl ester

Conditions	Yield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide at 25℃; pH 9;	A n/a B 67%

L-phenylalanine (63-91-2) + (4-acetoxyphenyl)-dimethylsulphonium methyl sulphate (108965-56-6) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With triethylamine In water for 4h; Ambient temperature; pH=10.0;	63%

L-Lysine ethyl ester (4117-33-3) + ethyl N-acetyl-(L)-phenylalaninate (2361-96-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid ethyl ester

Conditions	Yield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide pH 9;	A n/a B 53%
With α-chymotrypsin at 25℃; for 0.05h; Product distribution; various buffer and pH;

ethyl N-acetyl-DL-phenylalaninate (4134-09-2) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (R)-ethyl N-acetylphenylalanine (2361-96-8, 4134-09-2, 57772-79-9, 20918-84-7)

Conditions	Yield
With ammonium bicarbonate; water In dichloromethane for 18h; α-chymotrypsin;	A 50% B 50%
	A 50% B 50%
In ethanol; water at 35℃; for 48h; Yield given;

ethyl N-acetyl-DL-phenylalaninate (4134-09-2) → (R)-N-acetylphenylalanin (10172-89-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (R)-ethyl N-acetylphenylalanine (2361-96-8, 4134-09-2, 57772-79-9, 20918-84-7)

Conditions	Yield
With water In ethanol at 25℃; for 2h; Microbiological reaction; optical yield given as %ee; enantioselective reaction;	A n/a B n/a C 45%
at 35℃; for 48h; in the present of Saccharomyces cerevisiae Hansen; Yield given. Yields of byproduct given;

lysine benzyl ester p-toluenesulfonate salt (42406-73-5) + ethyl N-acetyl-(L)-phenylalaninate (2361-96-8) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid benzyl ester

Conditions	Yield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide at 25℃; pH 9;	A n/a B 31%

(R,S)-N-acetyl phenylalanine (2901-75-9) + (1S)-endo-fenchylamine (131348-01-1) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

(R,S)-N-acetyl phenylalanine (2901-75-9) + (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (119-62-0, 716-61-0, 2792-51-0, 2792-52-1, 2964-48-9, 3689-55-2, 63526-31-8, 71115-69-0, 140694-64-0) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

L-tyrosine (60-18-4) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
Reaktion ueber mehrere Stufen;

2-methyl-4-benzyl-4H-oxazolin-5-one (5469-44-3) → (R)-N-acetylphenylalanin (10172-89-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With alpha cyclodextrin In water; acetonitrile pH 7.86; Title compound not separated from byproducts;

2-(N-acetylamino)cinnamic acid (55065-02-6, 64590-80-3, 5469-45-4) → (R)-N-acetylphenylalanin (10172-89-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
With hydrogen In methanol at 25℃; under 3150.3 Torr; for 4h; Product distribution; enantioselectivity of reaction dependent on various rhodium complexes with 1,2-bis(phosphanyl)pyrrolidine ligands; various conditions; also N-acetylcinnamic acid methylester;
With 2S-MeN(PPh2)CHC7H7CH2OPPh2; hydrogen; Rh<(COD)Cl>2 Product distribution; other reagents;
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Br>n In ethanol at 20℃; Product distribution; asymmetric catalytic hydrogenation, enantiodifferentiating ability of the catalysts: atmospheric pressure of H2; var. catalysts, pressure, temp. and initial rate;

ethyl N-acetyl-DL-phenylalaninate (4134-09-2) → (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Conditions	Yield
In water α-chymotrypsin, 0.05 M phosphate buffer pH 7.4;

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → (S)-2-acetylamino-3-cyclohexylpropionic acid (100400-96-2, 97290-54-5)

Conditions	Yield
With platinum(IV) oxide; hydrogen; acetic acid In methanol under 2585.81 Torr; for 24h;	100%
With hydrogen; rhodium on alumina In methanol for 56h; Ambient temperature; Pressure (range begins): 2.5 ;	98.1%
With C33H49ClNRh; hydrogen In 2,2,2-trifluoroethanol at 20℃; under 45004.5 Torr; for 24h; Autoclave; Molecular sieve;	93%
With acetic acid; platinum Hydrogenation;
With sodium tetrahydroborate; rhodium(III) chloride 30 deg C, water, pH=4; Yield given. Multistep reaction;

2-hydroxy-1,1,2-trimethylpropyl ethylcarbamate (743477-27-2) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → 4,4,5,5-tetramethyl-1,3-dioxolan-2-one (19424-29-4) + ethyl N-acetyl-(L)-phenylalaninate (2361-96-8)

Conditions	Yield
With tert.-butylnitrite; 3 A molecular sieve In dichloromethane at 60℃; for 12h;	A n/a B 100%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + ethyl-(2-hydroxy-ethyl)-dimethyl-ammonium; hydroxide (76290-84-1) → C6H16NO(1+)*C11H12NO3(1-)

Conditions	Yield
In water at 20℃;	100%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + C7H18NO(1+)*HO(1-) → C11H12NO3(1-)*C7H18NO(1+)

Conditions	Yield
In water at 20℃;	100%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + butyl(2-hydroxyethyl)dimethylammonium hydroxide (114380-13-1) → C11H12NO3(1-)*C8H20NO(1+)

Conditions	Yield
In water at 20℃;	100%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + C9H22NO(1+)*HO(1-) → C11H12NO3(1-)*C9H22NO(1+)

Conditions	Yield
In water at 20℃;	100%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + ethyl iodide (75-03-6) → ethyl N-acetyl-(L)-phenylalaninate (2361-96-8)

Conditions	Yield
With caesium carbonate In acetonitrile for 1.5h; Heating;	99%
With cesium fluoride In N,N-dimethyl-formamide at 15℃; for 24h;	90%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → N-acetyl-L-phenylalanine N-hydroxysuccinimide ester (55604-95-0)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 3.5h;	99%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃;	85%
With dicyclohexyl-carbodiimide at 0 - 20℃;

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + L-phenylalanine tert-butyl ester hydrochloride (15100-75-1) → N-Acetylphenylalanylphenylalanine tert-butyl ester (128992-42-7)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 23h;	99%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + rhodium (378784-00-0, 7440-16-6) → (S)-2-acetylamino-3-cyclohexylpropionic acid (100400-96-2, 97290-54-5)

Conditions	Yield
In methanol	98.1%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → L-phenylalanine (63-91-2)

Conditions	Yield
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;	98%
With hydrogenchloride
With hydrogen bromide

2-iodo-propane (75-30-9) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → isopropyl α-acetylamido-3-phenylpropanoate

Conditions	Yield
With caesium carbonate In acetonitrile for 1.5h; Heating;	98%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (R)-mandelic acid ethyl ester (10606-72-1) → (R)-2-Acetylamino-3-phenyl-propionic acid (S)-ethoxycarbonyl-phenyl-methyl ester

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 6h; Mitsunobu reaction;	98%

1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → C14H13F6NO3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4.5h;	96%

methanol (67-56-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → (S)-N-acetylphenylalanine (3618-96-0)

Conditions	Yield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride	95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 20h;	95%
With N-Bromosuccinimide at 70℃; for 20h;	91%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → N-acetyl-L-phenylalanyl-L-phenylalanine methylester (2562-48-3)

Conditions	Yield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride	95%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h;	53%
With sodium hydroxide; thermolysin at 37℃; for 24h; pH=6.3; enzymatic amidation;

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + 2-amino-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester (849770-98-5) → (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester

Conditions	Yield
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	95%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + silver(l) oxide (20667-12-3) → [Ag((S)-N-acetylphenylalanate)]

Conditions	Yield
In acetonitrile slurry (S)-N-acetylphenylalanine in MeCN was added to slid Ag2O and stirred for 24 h in the dark; ppt. was filtered off, washed with Et2O, and dried in vacuo; elem. anal.;	95%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → (L)-N-acetyl-phenylalanine vinyl ester (147092-06-6)

Conditions	Yield
With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine In tetrahydrofuran at 50℃; for 16h; Chan-Lam Coupling;	94%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + chloroacetonitrile (107-14-2) → (S)-cyanomethyl 2-acetamido-3-phenylpropanoate (61781-58-6)

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 4.5h;	93%
With N-ethyl-N,N-diisopropylamine for 12h;	90%
With N-ethyl-N,N-diisopropylamine for 12h;	90%
With triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;	89%
With triethylamine

Upstream product

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• 201860-40-4 H-THR(TBU)-AMC HCL 
• 201860-29-9 SUC-TYR-VAL-ALA-ASP-AMC 
• 201860-17-5 BACLIGHT(TM) GREEN BACTERIAL STAIN 
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• 201858-22-2 2-(4-chloroanilino)-4-oxo-4-phenylbutanoic acid 
• 201857-39-8 4-AMINO-3-BROMO-5-CHLOROBENZONITRILE 
• 201856-57-7 (3R,4S)-tert-Butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate 
• 201856-567-7 (3R,4S)-1-AzetidinecarboxylicAcid-3-(2-Ethoxyethoxy)-4-Phenyl-2-Phenyl-AzetidioneCasNo. 
• 201856-53-3 (3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone 
• 201856-48-6 (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone 
• 201855-71-2 trans 1-Benzyl-4-(4-fluorophenyl)-3-methylsulfonatepiperidine 
• 201855-60-9 trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol 

Downstream Products

• 201861-91-8 4,4''-DIIODO-TRANS-STILBENE 
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