Water → 7beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester

HRID 126905

Reaction equation

HRID 126905 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:26])=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(N(CC)CC)C.[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37](Br)[O:36]1)=[O:35].O>CN(C)C=O>[C:34]1([C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]([O:19][C:18]([C:14]2[N:13]3[C:21](=[O:22])[C@@H:11]([NH:10][C:8](=[O:9])[C:7]([C:5]4[N:6]=[C:2]([NH2:1])[S:3][C:4]=4[Cl:26])=[N:23][O:24][CH3:25])[C@H:12]3[S:17][CH2:16][CH:15]=2)=[O:20])[O:36]1)=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 1317121027beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317121087beta-[2-(2-Amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (209 mg) in N,N-dimethylformamide (5 ml) are added triethylamine (0.07 ml) and phthalidyl bromide (128 mg), and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is poured into water and the separated precipitate is collected by filtration. The solid material is dissolved in ethyl acetate, washed with water, diluted aqueous sodium hydrogen carbonate solution, water, diluted aqueous phosphoric acid and water, dried, and evaporated. Purification of the residue by silica gel column chromatography gives 7β-[2-(2-amino-5-chloro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid phthalidyl ester (220 mg).

Workup

  1. filtrationthe separated precipitate is collected by filtration
  2. dissolutionThe solid material is dissolved in ethyl acetate
  3. washwashed with water, diluted aqueous sodium hydrogen carbonate solution, water, diluted aqueous phosphoric acid and water
  4. customdried
  5. customevaporated
  6. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-4e3ef60a8e184445b7789b10ae164850
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Linked notes

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