Formic Acid → HCID 53939500, compound

HRID 1660400Notes

Reaction equation

HRID 1660400 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:49][O:50][CH3:51])[C:8]([NH:10][CH:11]2[C:18](=[O:19])[N:17]3[CH:12]2[S:13][CH2:14][C:15]([CH:36]=[CH:37][O:38][S:39]([C:42]2[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=2)(=[O:41])=[O:40])=[C:16]3[C:20]([O:22]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:21])=[O:9])[N:6]=1.C(O)=O.O>C(OCC)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:49][O:50][CH3:51])[C:8]([NH:10][CH:11]2[C:18](=[O:19])[N:17]3[CH:12]2[S:13][CH2:14][C:15]([CH:36]=[CH:37][O:38][S:39]([C:42]2[CH:43]=[CH:44][C:45]([CH3:46])=[CH:47][CH:48]=2)(=[O:40])=[O:41])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962Water2×HCID 53704037HCID 53704037, compound

Product 1

HCID 53939500HCID 53939500, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-[2-(2-amino-thiazol-4-yl)-2-methoxyimino-acetamido]-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxy-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, E-form) (0.35 g), formic acid (10 cc) and water (3 cc) is stirred at 50° C. for 30 minutes. Water (8 cc) is then added and the mixture is filtered and concentrated to dryness at 30° C. under 0.05 mm Hg (0.007 kPa). The residue is taken up in ethanol (2×20 cc), each time concentrating the mixture to dryness at 20° C. under 20 mm Hg (2.7 kPa). The solid obtained is trituranted in diethyl ether (20 cc). After filtration ad drying, 7-[2-(2-amino-thiazol-4-yl)-2-methoxyimino-acetamido]-2-carboxy-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, E-form) (0.12 g) is obtained in the form of yellow powder.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationconcentrated to dryness at 30° C. under 0.05 mm Hg (0.007 kPa)
  3. concentrationeach time concentrating the mixture to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  4. customThe solid obtained
  5. filtrationAfter filtration ad
  6. customdrying

Sources & evidence

ORD record
ord-759b863b062543b791a228718d8da96b
Source dataset
uspto-grants-1981_12
Patent number
US04307230

Reaction notes

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