(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → HCID 131710507, compound

HRID 1288439Notes

Reaction equation

HRID 1288439 reaction equation
[O:1]([CH:8]([CH3:12])[C:9]([O-:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[NH2:14][CH:15]1[C:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]12>>[O:1]([CH:8]([CH3:12])[C:9]([NH:14][CH:15]1[C:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]12)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 23702052HCID 23702052, compound

Product 1

HCID 131710507HCID 131710507, compound

Procedure

The procedure of Example 1 was repeated using 1.9 g of lithium α-phenoxypropionate and 2.14 g of 7-amino-3-methyl-3-cephem-4-carboxylic acid. 7-(α-Phenoxypropionamido)-3-methyl-3-cephem-4-carboxylic acid was obtained as a colorless crystalline product in a yield of 3.22 g (95%, mp. 145° C (dec.). This product showed the infra-red and ultra-violet absorption spectra which were entirely coincident with those of the authentic sample.

Sources & evidence

ORD record
ord-74d4addbcdf64211988ab753005cc5b1
Source dataset
uspto-grants-1976_10
Patent number
US03988326

Reaction notes

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