Water → HCID 70524291, compound

HRID 1902517Notes

Reaction equation

HRID 1902517 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]1([CH2:14][C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[CH:21]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH:22]([CH2:25][OH:26])[CH2:23][S:24][C@H:19]23)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.C(OCC)(=O)C>CS(C)=O>[C:8]1([CH2:14][C:15]([NH:17][CH:18]2[C:43](=[O:44])[N:20]3[CH:21]([C:27]([O:29][CH:30]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:28])[C:22](=[CH:25][O:26][C:1](=[O:3])[CH3:2])[CH2:23][S:24][C@H:19]23)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 70524691HCID 70524691, compound

Product 1

HCID 70524291HCID 70524291, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Acetic anhydride (20 ml.) was added to a solution of diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (10.0 g.) in dimethylsulfoxide (20 ml.), and stirred at room temperature for 15 hours. The resultant solution was poured into a solution of water (400 ml.) and ethyl acetate (400 ml.). The organic layer was separated and adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. The solution was concentrated under reduced pressure to give diphenylmethyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (5.3 g.).

Workup

  1. customThe organic layer was separated
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9406e5b0c79e4ec9ba54c2db5f5f8f09
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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