ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamate → (S)-alpha-[[(Cyclopropylmethyl)sulphonyl]methyl]hydrocinnamic acid

HRID 2294744Notes

Reaction equation

HRID 2294744 reaction equation
[CH:1]1([CH2:4][S:5]([CH2:8][CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(S(CC(CC1C=CC=CC=1)C(OCC)=O)(=O)=O)(C)(C)C>>[CH:1]1([CH2:4][S:5]([CH2:8][C@@H:9]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]([OH:12])=[O:11])(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 14158057ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamateHCID 86751664ethyl (RS)-alpha-[[(cyclopropylmethyl)sulphonyl]methyl]hydrocinnamate

Product 1

HCID 86751663(S)-alpha-[[(Cyclopropylmethyl)sulphonyl]methyl]hydrocinnamic acid

Procedure

This compound was prepared analogously to Example 1d) by the enzymatic hydrolysis of ethyl (RS)-α-[[(cyclopropylmethyl)sulphonyl]methyl]hydrocinnamate which, in turn, was prepared analogously to the synthesis of ethyl (RS)-α-[(tert-butylsulphonyl)methyl]hydrocinnamate described in EPA 0236734 by replacing tert-butylthiol by cyclopropylmethylthiol, MS: 282 (M)+.

Workup

  1. customThis compound was prepared analogously to Example 1d)

Sources & evidence

ORD record
ord-552370714889440da57331d7957e730b
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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