Potassium ethanethioate → (3s,5r)-Thioacetic acid s-[5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl] ester
Reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[N:14]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(=[O:17])=[O:16])[CH2:13][C@@H:12](OS(C)(=O)=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([O-:36])(=[S:35])[CH3:34].[K+]>CN(C=O)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[N:14]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(=[O:17])=[O:16])[CH2:13][C@@H:12]([S:35][C:33](=[O:36])[CH3:34])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of (3S,5S)-methanesulfonic acid 5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl ester (3.0 g) in abs DMF (60 ml) was added potassium thioacetate (1.08 g). The reaction mixture was stirred for 1 h at 100° C. and concentrated under oil pump vacuum. The residue was treated with ice/water and extracted with EtOAc. The organic phase was washed with water and brine, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:3 as eluent to obtain (3S,5R)-thioacetic acid S-[5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl]ester (2.16 g) as a slightly yellow powder, MS: 334 (M−121).
Workup
- concentrationconcentrated under oil pump vacuum
- additionThe residue was treated with ice/water
- extractionextracted with EtOAc
- washThe organic phase was washed with water and brine
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-954f41e952b44e4e895bf0592b9c447b
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790860B2
Reaction notes
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