Potassium ethanethioate → HCID 57142678, compound

HRID 2293795Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1F)[C@@H:10](OS(C1C=CC(C)=CC=1)(=O)=O)[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]([O-:36])(=[S:35])[CH3:34].[K+]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:10]([S:35][C:33](=[O:36])[CH3:34])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 23670855Potassium ethanethioate

HCID 57286434HCID 57286434, compound

Product 1

HCID 57142678HCID 57142678, compoundYield 43.2%

Procedure

Methyl (2RS,3S)-3-tert-butoxycarbonylamino-2-acetylthio-3-(2-fluorophenyl) propionate may be prepared in a similar manner to that described in Example 1G, but starting with 30 g of methyl (2R,3S)-3-tert-butoxycarbonylamino-2-tosyloxy-3-(2-fluorophenyl)propionate and 17.2 g of potassium thioacetate. 9.8 g of methyl (2RS,3S)-3-tert-butoxycarbonylamino-2-acetylthio-3-phenylpropionate are thus obtained in the form of a red oil which is used without further purification in the subsequent syntheses.

Sources & evidence

ORD record: ord-27c65cdbc44140ceb075bf473a42a494
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686622

Reaction notes

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