Sodium nitrite hydrate → HCID 178427241, compound

HRID 1155151Notes

Reaction equation

HRID 1155151 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:5]2[C:16](=[O:26])[CH:17]([NH:18][C:19](=[O:25])[CH2:20][C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1.O.[N:28]([O-])=[O:29].[Na+]>C(O)(=O)C.O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][C:12]([Cl:13])([Cl:15])[Cl:14])=[O:9])[N:5]2[C:16](=[O:26])[CH:17]([NH:18][C:19](=[O:25])[C:20](=[N:28][OH:29])[C:21](=[O:24])[CH2:22][Br:23])[C@H:4]2[S:3]1

Participants

5

Reactant 2

HCID 23686037Sodium nitrite hydrateHCID 1317114902,2,2-Trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate

Product 1

HCID 178427241HCID 178427241, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (2.54 g.) in glacial acetic acid (25 ml.) was added dropwise a solution of sodium nitrite hydrate (0.33 g.) in water (1 ml.) over 3 minutes with stirring at 10° to 15° C., and then the mixture was stirred for 1 hour at the same temperature. After the reaction mixture was poured into cold water (70 ml.), the precipitates were collected by filtration and then dried to give brown powder of 2,2,2-trichloroethyl 2-methyl-7-(2-hydroxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylate (a mixture of syn and anti isomers) (2.0 g.), mp 76° to 80° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. filtrationthe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-203c05407efa4744905610842f481c08
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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