Water → HCID 70523908, compound

HRID 1902507Notes

Reaction equation

HRID 1902507 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[C:6]1([CH2:12][C:13]([NH:15][CH:16]2[C:32](=[O:33])[N:18]3[CH:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:20]([CH:23]=O)[CH2:21][S:22][C@H:17]23)=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[C:6]1([CH2:12][C:13]([NH:15][CH:16]2[C:32](=[O:33])[N:18]3[CH:19]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[C:20](=[CH:23][O:3][C:1](=[O:4])[CH3:2])[CH2:21][S:22][C@H:17]23)=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 86738681HCID 86738681, compound

Product 1

HCID 70523908HCID 70523908, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Anhydrous sodium acetate (1.0 g.) was added to a solution of t-butyl 7-(2-phenylacetamido)-3-formylcepham-4-carboxylate (2.0 g.) in acetic anhydride (5 ml.) and stirred at 65° to 70° C. for an hour. To the resultant solution were added water (200 ml.) and ethyl acetate (200 ml.), and adjusted to pH 8.0. The organic layer was separated, washed with aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to give t-butyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (1.6 g.), mp. 178° to 183° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2a01410a52554c5ca2c4aa4158fc5398
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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