Sodium Chloride → 3-Acetoxymethyl-7-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

HRID 257809Notes

Reaction equation

HRID 257809 reaction equation
N[C@H:2]1[C:21](=[O:22])[N:4]2[C:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12.N([O-])=O.[Na+].[Cl-:27].[Na+]>C(O)C.O.Cl>[Cl:27][C@H:2]1[C:21](=[O:22])[N:4]2[C:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 15573428t-Butyl 7alpha-amino-3-acetoxymethyl-3-cephem-4-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 157268683-Acetoxymethyl-7-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl esterYield 73%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To an ice-cooled solution of t-butyl 7α-amino-3-acetoxymethyl-3-cephem-4-carboxylate (4.0 g, 0.0122 mol) in 75 ml of ethanol, 16.7 ml of water and 16.7 ml of concentrated hydrochloric acid was added portionwise over 15-20 minutes sodium nitrite (1.18 g, 0.017 mol). The reaction mixture was stirred at 0°-5° C. for 2.5 hours, saturated with sodium chloride, extracted with methylene chloride, washed with water, brine, dried Na2SO4 and concentrated to give 3.1 g (73%) of t-butyl 7α-chloro-3-acetoxymethyl-3-cephem-4carboxylate.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water, brine, dried Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5ea4deb4eb244ca0bc20dba16d05ea6a
Source dataset
uspto-grants-1993_11
Patent number
US05264430

Reaction notes

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