Water → HCID 131713931, compound

HRID 1632764Notes

Reaction equation

HRID 1632764 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O-:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:27]1([C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](=[CH:37][CH2:38]Br)[O:29]1)=[O:28].O.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH2:38][CH:37]=[C:30]4[C:31]5[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=5)[C:27](=[O:28])[O:29]4)=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 54475276HCID 54475276, compoundHCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 131713931HCID 131713931, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer) (1.4 g) in N,N-dimethylformamide (40 ml) was added 3-phthalidylideneethyl bromide (1.0 g), and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was poured into a mixture of water and ethyl acetate (each 200 ml) with stirring. The separated organic solution was washed with 5% aqueous sodium bicarbonate and then water, followed by drying over magnesium sulfate. The resultant solution was evaporated to dryness to give 2-(3-phthalidylidene)ethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer) (1.5 g), mp 150° to 156° C. (dec.).

Workup

  1. stirringwith stirring
  2. washThe separated organic solution was washed with 5% aqueous sodium bicarbonate
  3. dry with materialby drying over magnesium sulfate
  4. customThe resultant solution was evaporated to dryness

Sources & evidence

ORD record
ord-dd09743f71d247649892e554425649ae
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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