Hydrogen Bromide → HCID 68131788, compound

HRID 1287996Notes

Reaction equation

HRID 1287996 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)(=O)C.[BrH:27].C(Cl)Cl>>[Br:27][CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:26])[CH:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 68131832HCID 68131832, compound

Product 1

HCID 68131788HCID 68131788, compound

Procedure

A cooled solution (in ice) of benzyl ester of 3-acetoxymethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid (77 mg., 0.15 mmole) is stirred while hydrogen bromide (0.5 ml.) in methylene chloride (0.32 mmole) is added dropwise. The reaction is stopped 50 minutes later by simply bubbling off the excess hydrogen bromide with nitrogen. Removal of the solvent affords the benzyl ester of 3-bromomethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid which is employed directly in Step C.

Workup

  1. additionis added dropwise
  2. customlater by simply bubbling off the excess hydrogen bromide with nitrogen
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-6c52a5d105d9411c95ee1598c3a01b88
Source dataset
uspto-grants-1976_10
Patent number
US03987040

Reaction notes

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