Sodium Bicarbonate → 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 256438Notes

Reaction equation

HRID 256438 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([Br:39])=[C:7]([C:9](=[N:36][O:37][CH3:38])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:31]([OH:33])=[O:32])=[C:17]([CH2:20][O:21][C:22](=[O:30])[NH:23]C(=O)C(Cl)(Cl)Cl)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].C(=O)(O)[O-].[Na+]>CO>[CH:1]([NH:3][C:4]1[S:5][C:6]([Br:39])=[C:7]([C:9](=[N:36][O:37][CH3:38])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:31]([OH:33])=[O:32])=[C:17]([CH2:20][O:21][C:22](=[O:30])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 1317153467-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153477-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acidYield 62.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 1.9 g.) was added to an aqueous solution (80 ml.) of sodium bicarbonate (225 mg.), and adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. Methanol (4 ml.) was added to the solution and stirred at room temperature for 2.5 hrs. The reaction mixture was adjusted to pH 7.5 and washed with ethyl acetate. The aqueous solution was adjusted to pH 2.0 with 6N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diethyl ether and dried to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 0.95 g.).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washThe residue was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-50caa87733364b84957a72926f45e4f3
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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