Benzyl mercaptan → (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:7])[C@H:4]1[O:6][CH2:5]1.[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([OH:6])[CH2:5][S:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7509Benzyl mercaptan

HCID 10942355Methyl (2S)-2-oxiranecarboxylate

Product 1

HCID 59639322(R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl esterYield 92%

Procedure

This reaction was performed as previously described by Deechongkit, S.; You, S.-L.; Kelly, J. W. Org. Lett. 2004, 6, 497, using (S)-Methylglycidate 110a and Benzyl mercaptan. (R)-3-Benzylsulfanyl-2-hydroxy-propionic acid methyl ester 110b (7.41 g, 31.41 mmol, 92%) was isolated as a viscous oil: MS calcd. for C11H14O3S (M+H+) 227.1, found 227.3.

Sources & evidence

ORD record: ord-27bc3950df9e4290b5641d3488fcb1c7
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732449B2

Reaction notes

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