Potassium ethanethioate → HCID 86584853, compound

HRID 458353Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11](Cl)[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([O-:29])(=[S:28])[CH3:27].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([S:28][C:26](=[O:29])[CH3:27])[CH2:10][C@@H:9]1[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 0.873 mg (2 mmol) (2S,4S)-4-chloro-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was dissolved in 20 ml DMF and after the addition of 0.343 mg (3 mmol) potassium thioacetate heated for 2.5 h at 100° C. Evaporation and flash-chromatography on silica gel (toluene/CH3CN 95:5) gave 0.745 g (89%) of (2R,4S)-4-acetylsulfanyl-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 420 (MH+).

Workup

customEvaporation and flash-chromatography on silica gel (toluene/CH3CN 95:5)

Sources & evidence

ORD record: ord-c65d9ac318e8463e8189f140195be8c3
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189756B2

Reaction notes

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