2-[(Acetylthio)methyl]-3-phenylpropionic Acid → N-[1-Hydroxy-3-phenyl-2-(sulfanylmethyl)propylidene]leucine

HRID 1003955Notes

Reaction equation

HRID 1003955 reaction equation
C[O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH:22]([CH3:24])[CH3:23])[NH:5][C:6](=[O:20])[CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][S:9]C(=O)C.C(SCC(CC1C=CC=CC=1)C(O)=O)(=O)C>>[CH2:13]([CH:7]([CH2:8][SH:9])[C:6]([NH:5][C@H:4]([C:3]([OH:25])=[O:2])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 21967978HCID 21967978, compound

Product 1

HCID 133576N-[1-Hydroxy-3-phenyl-2-(sulfanylmethyl)propylidene]leucineYield 81%

Procedure

N-[S-Acetyl-2'-benzyl-3'-mercaptopropionyl]leucine methyl ester Prepared by Method B of Example 19 but on a 1:1 mixture of D and L-leucine methyl ester hydrochlorides (113 mg, 0.5 mmol, L isomer from Aldrich) and using S-acetyl-2-benzyl-3-mercaptopropionic acid (0.5 mmol). This gave the title compound as a clear oil in 81% yield, an approximately equimolar mixture of diastereoisomers. These were partially separated.

Sources & evidence

ORD record
ord-976c88ae56c14898b765f4d71e287a26
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

Loading…