ammonium (6R,7R)-3-acetoxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate → (6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 261150Notes

Reaction equation

HRID 261150 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=[O:3])C.[NH4+:30]>CO>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:30]

Participants

3

Reactant 1

HCID 131711594ammonium (6R,7R)-3-acetoxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate

Product 1

HCID 41375(6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The process was repeated with ammonium (6R,7R)-3-acetoxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) (40 mg) as substrate and with the addition of pig liver acetylesterase (1 unit). Analysis of the product by TLC (silicachloroform/methanol/90% formic acid - 90:16:4) showed the presence of a new u.v. absorbing spot with an identical Rf to the standard sample of title compound.

Workup

  1. customabsorbing spot with an identical Rf to the standard sample of title compound

Sources & evidence

ORD record
ord-31739aad34d5403980ed76b7143afef2
Source dataset
uspto-grants-1979_08
Patent number
US04164447

Reaction notes

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