Ethyl Acetate → HCID 70524291, compound

HRID 1902511Notes

Reaction equation

HRID 1902511 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[C:6]1([CH2:12][C:13]([NH:15][CH:16]2[C:41](=[O:42])[N:18]3[CH:19]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[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.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C.O>[C:6]1([CH2:12][C:13]([NH:15][CH:16]2[C:41](=[O:42])[N:18]3[CH:19]([C:25]([O:27][CH:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[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

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86738682HCID 86738682, compound

Product 1

HCID 70524291HCID 70524291, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium acetate (0.23 g.) was added to a solution of diphenylmethyl 7-(2-phenylacetamido)-3-formylcepham-4-carboxylate (0.5 g.) in acetic anhydride (2 ml.), and stirred at 50° C. for 1.5 hours. The resultant solution was added to ethyl acetate (60 ml.) and water (50 ml.) and adjusted to pH 7.2 with sodium bicarbonate. The organic layer was separated, washed with aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was evaporated in vacuo to give diphenylmethyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (0.4 g.).

Workup

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

Sources & evidence

ORD record
ord-d43a6f2f776d40fd88620453d486400b
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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