Acetic Acid → HCID 178520134, compound

HRID 435014Notes

Reaction equation

HRID 435014 reaction equation
[Br:1][CH2:2][C:3]([CH2:5][C:6]([NH:8][CH:9]1[C:29](=[O:30])[N:11]2[C:12]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])=[CH:13][CH2:14][S:15][C@H:10]12)=[O:7])=[O:4].C(O)(=O)C.[N:35]([O-])=[O:36].[Na+]>O1CCCC1.O>[Br:1][CH2:2][C:3]([C:5](=[N:35][OH:36])[C:6]([NH:8][CH:9]1[C:29](=[O:30])[N:11]2[C:12]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[O:17])=[CH:13][CH2:14][S:15][C@H:10]12)=[O:7])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 886077454-Nitrobenzyl 7-[2-(2-bromoacetyl)acetamido]-3-cephem-4-carboxylate

Product 1

HCID 178520134HCID 178520134, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl 7-[2-(2-bromoacetyl)acetamido]-3-cephem-4-carboxylate (8.40 g.) was suspended in a mixture of tetrahydrofuran (150 ml.) and water (30 ml.) To the suspension were added acetic acid (50 ml.) and a solution of sodium nitrite (1.20 g.) in water (15 ml.) under ice-cooling, and stirred at 20° to 22° C. for 1.5 hours. The resultant solution was poured into ice-water (300 ml.) and stirred for 20 minutes. The precipitating substance was collected by filtration, washed with water, dried and then recrystallized from ethyl acetate to give 4-nitrobenzyl 7-[2-(2-bromoacetyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 3.1 g.), mp 153° to 162° C.

Workup

  1. stirringstirred for 20 minutes
  2. filtrationThe precipitating substance was collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1aec3086c6884226a235722b1c466091
Source dataset
uspto-grants-1983_08
Patent number
US04399133

Reaction notes

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