HCID 86739897, compound → HCID 86739896, compound

HRID 2413436Notes

Reaction equation

HRID 2413436 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2[CH2:17][O:16][CH:15]3[N:12]([C:13](=[O:23])[CH:14]3[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:11]=2[NH:24][C:25](=[O:43])[CH2:26][C:27]([O:29]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2]>C(O)=O.C(O)C>[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2[CH2:17][O:16][CH:15]3[N:12]([C:13](=[O:23])[CH:14]3[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:11]=2[NH:24][C:25](=[O:43])[CH2:26][C:27]([OH:29])=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86739897HCID 86739897, compound

Product 1

HCID 86739896HCID 86739896, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 3-(2-acetylamino-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2-yl)-acetamido-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.1 g) in formic acid (5 cc) is heated at 50° C. for 30 minutes, with stirring. The mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C., and the residue is dissolved in ethanol (5 cc). The suspension obtained is stirred at 50° C. for 5 minutes and the solvent is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 50° C.; this operation is repeated once, and the residue thus obtained is taken up in ethanol (2 cc). The solid in suspension yields, on filtration, 3-(2-acetylamino-thiazol-5-yl)-2-carboxy-8-oxo-7-(thien-2-yl)-acetamido-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (12 mg) in the form of a beige powder.

Workup

  1. concentrationThe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.
  2. dissolutionthe residue is dissolved in ethanol (5 cc)
  3. customThe suspension obtained
  4. stirringis stirred at 50° C. for 5 minutes
  5. customthe solvent is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 50° C.
  6. customthe residue thus obtained

Sources & evidence

ORD record
ord-449b9b954e0a41d6b56522c7aa8408c2
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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