Phenylalanine ethyl ester → (+/-)-N-[2-(acetylthiomethyl)-4-methyl-1-oxopentyl]-L-phenylalanine, ethyl ester

HRID 1440073Notes

Reaction equation

HRID 1440073 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[NH2:14][C@H:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([NH:14][C@H:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 76506Phenylalanine ethyl esterHCID 81531DiisopropylethylamineHCID 127690742-[(Acetylthio)methyl]-4-methylpentanoyl chloride

Product 1

HCID 131719290(+/-)-N-[2-(acetylthiomethyl)-4-methyl-1-oxopentyl]-L-phenylalanine, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Acetylthiomethyl-4-methylpentanoyl chloride and (L)-phenylalanine, ethyl ester are reacted in methylene chloride in the presence of diisopropylethylamine at a temperature below 0° according to the procedure of Example 26 to yield (±)-N-[2-(acetylthiomethyl)-4-methyl-1-oxopentyl]-L-phenylalanine, ethyl ester as an off-white foam.

Sources & evidence

ORD record
ord-8ea3a47c04da488ebb8bb1a1a7a082df
Source dataset
uspto-grants-1996_03
Patent number
US05496805

Reaction notes

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