Methanol → HCID 22867587, compound

HRID 1902142Notes

Reaction equation

HRID 1902142 reaction equation
[Si]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[S:18])[CH3:16])[NH:13][C:12]1=[O:26])[CH3:10])(C(C)(C)C)(C)C.CO.Cl[Si](C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[S:18])[CH3:16])[NH:13][C:12]1=[O:26])[CH3:10]

Participants

6

Reactant 3

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 57085400HCID 57085400, compound

Product 1

HCID 22867587HCID 22867587, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S ,4S)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-[(1R)-1-p-chlorophenylthiocarbonylethyl]-2-azetidinone (1.29 g, 3.0 mmol) is dissolved in toluene (10 ml), and thereto are added methanol (2 ml) and chlorotrimethylsilane (0.1 ml). The mixture is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate (50 ml), washed several times with brine, dried over magnesium sulfate, and evaporated to remove the solvent to give (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)- 1-p-chlorophenylthiocarbonylethyl]-2-azetidinone (627 mg).

Workup

  1. washwashed several times with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto remove the solvent

Sources & evidence

ORD record
ord-c02e84593b84488b89782723f56d5f93
Source dataset
uspto-grants-1996_11
Patent number
US05578722

Reaction notes

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