Hydrochloric Acid → HCID 131711061, compound

HRID 1679697Notes

Reaction equation

HRID 1679697 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:34](=[O:35])[N:13]3[C:14]([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=4)=[O:22])=[C:15]([Cl:20])[CH:16]([CH3:19])[S:17](=O)[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C.Cl.C(OCC)(=O)C>CN(C)C=O.O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:34](=[O:35])[N:13]3[C:14]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=4)=[O:22])=[C:15]([Cl:20])[CH:16]([CH3:19])[S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 70616771HCID 70616771, compound

Product 1

HCID 131711061HCID 131711061, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Nmr: δd 6-DMSO : 1.36d(8.0Hz)3H, 3.62s2H, 3.93q(8.0Hz)1H, 4.90d(5.0Hz)1H, 5.40s2H, 5.87dd(5.0;8.0Hz)1H, 7.2-8.4m1OH. (II) To a solution of p-nitrobenzyl 7-phenylacetamido-2-methyl-3-chloro-3cephem-4-carboxylate-1-oxide (38 mg) in dimethylformamide (2 ml) one adds stannous chloride dihydrate (44 mg) and acetyl chloride (0.2 ml), stirs for 3hours under ice cooling, adds 5% hydrochloric acid, extracts with ethyl acetate, washes with water, dries, and chromatographs on silica gel to give p-nitrobenzyl 7-phenylacetamido-2-methyl-3-chloro-3cephem-4-carboxylate (29 mg).

Sources & evidence

ORD record
ord-5967aaae777345b28eb8d9c3246d209a
Source dataset
uspto-grants-1978_03
Patent number
US04081595

Reaction notes

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