Acetate → HCID 131712814, compound

HRID 2296556Notes

Reaction equation

HRID 2296556 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])=[C:3]1[CH3:18].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C([O-])(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:25]([O:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:15])[Cl:16])=[O:11])=[C:3]1[CH3:18])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 175AcetateHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131712812HCID 131712812, compound

Product 1

HCID 131712814HCID 131712814, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a freshly prepared solution of 2,2,2-trichloroethyl 1-hydroxy-2-methylcarbapen-2-em-3-carboxylate in methylene chloride, prepared from 100 mg. (0.317 mmole) of the 1-beta-oxide by Examples 11 and 12) was added 24 microl. (0.317 mmole) of pyridine, 29 microl. (0.317 mmole) of acetic anhydride and 4 mg. of 4-dimethylaminopyridine. Infrared spectral analysis indicated clean conversion to the desired acetate. Following water wash and drying, evaporation to dryness gave 2,2,2-trichloroethyl 1-acetoxy-2-methylcarbapen-2-em-3-carboxylate [ir (CH2Cl2) 1780, 1725, 1700 cm-1 ; Rf 0.7-0.75 (4:1 chloroform:ethyl acetate].

Workup

  1. washFollowing water wash
  2. customdrying
  3. customevaporation to dryness

Sources & evidence

ORD record
ord-d5af57b7a8504fa4ba770c82cc04e738
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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