HCID 13175963, compound → HCID 13175969, compound

HRID 2413406Notes

Reaction equation

HRID 2413406 reaction equation
[C:1]([NH:9][C:10]1[S:11][C:12]([C:15]2[CH2:22][S:21][CH:20]3[N:17]([C:18](=[O:32])[CH:19]3[NH:23][C:24](=[O:31])[CH2:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[C:16]=2[C:33]([O:35]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:34])=[CH:13][N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O>[C:1]([NH:9][C:10]1[S:11][C:12]([C:15]2[CH2:22][S:21][CH:20]3[N:17]([C:18](=[O:32])[CH:19]3[NH:23][C:24](=[O:31])[CH2:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[C:16]=2[C:33]([OH:35])=[O:34])=[CH:13][N:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 13175963HCID 13175963, compound

Product 1

HCID 13175969HCID 13175969, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(2-benzamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.5 g) in a mixture of formic acid (43 cc) and distilled water (8 cc) is heated for 30 minutes at 60° C. and then diluted with distilled water (35 cc). The precipitate is filtered off, washed with 50% strength (by volume) formic acid (2×10 cc) and then with isopropyl ether (3×75 cc) and dried; 3-(2-benzamidothiazol-5-yl)-2-carboxy-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1 g) is obtained in the form of a white solid.

Workup

  1. distillationdistilled water (8 cc)
  2. additiondiluted with distilled water (35 cc)
  3. filtrationThe precipitate is filtered off
  4. washwashed with 50% strength (by volume) formic acid (2×10 cc)
  5. dry with materialwith isopropyl ether (3×75 cc) and dried

Sources & evidence

ORD record
ord-aa081c9ee608475ba387acb6ea58e26b
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

Loading…