Acetic Anhydride → HCID 53785237, compound

HRID 597486Notes

Reaction equation

HRID 597486 reaction equation
[OH:1][C@H:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1.C(OC(=O)C)(=O)C>CS(C)=O>[O:1]=[C:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70638900HCID 70638900, compound

Product 1

HCID 53785237HCID 53785237, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(3S,6R,7R)-3-Hydroxy-7-phenylacetamidocepham (29 mg.) in dimethylsulphoxide (1 ml.) was treated with acetic anhydride (0.2 ml.) After being kept at 24° for 16 hour the reaction mixture was partitioned between brine and ethyl acetate. Removal of the ethyl acetate gave (6R,7R)-3-keto-7-phenylacetamidocepham (22 mg.). T.1.c. and g.1.c. data were in agreement with those obtained on material prepared in Example 3a. EXAMPLE 3d

Workup

  1. customthe reaction mixture was partitioned between brine and ethyl acetate
  2. customRemoval of the ethyl acetate

Sources & evidence

ORD record
ord-56d66c1436f444d5a1fdf2f5ac66b210
Source dataset
uspto-grants-1977_03
Patent number
US04014872

Reaction notes

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