Water → HCID 178508492, compound

HRID 1902977Notes

Reaction equation

HRID 1902977 reaction equation
FC(F)(F)C([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:32]([OH:34])=[O:33])=[C:19]([CH:22]([S:26][C:27]4[NH:31][N:30]=[N:29][N:28]=4)[CH2:23][CH2:24][OH:25])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=O.C([O-])(=O)C.[Na+].O>O1CCCC1>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43]2)[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:32]([OH:34])=[O:33])=[C:19]([CH:22]([S:26][C:27]4[NH:31][N:30]=[N:29][N:28]=4)[CH2:23][CH2:24][OH:25])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 178524399HCID 178524399, compound

Product 1

HCID 178508492HCID 178508492, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-[2-[2-(2,2,2-trifluoroacetamido)-thiazol-4-yl]-2-cyclopentyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 2.5 g.), sodium acetate 3 hydrate (4.9 g.), water (30 ml.) and tetrahydrofuran (14.0 ml.) was stirred at room temperature for 18 hours. After removing tetrahydrofuran from the resultant solution in vacuo, water (20 ml.) was added to the residue and adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 1.54 g.), mp. 150°-156° C. (dec.).

Workup

  1. customAfter removing tetrahydrofuran from the resultant solution in vacuo, water (20 ml.)
  2. additionwas added to the residue
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-b8156a1afc7b414181273da72ff9cad0
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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