Hydrochloric Acid → HCID 131713614, compound

HRID 1463102Notes

Reaction equation

HRID 1463102 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[N:35]=[C:36]([NH:39]C=O)[S:37][CH:38]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.O>[NH2:39][C:36]1[S:37][CH:38]=[C:34]([C:11](=[N:10][O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([NH:14][CH:15]2[C:32](=[O:33])[N:17]3[C:18]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]23)=[O:13])[N:35]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131713615HCID 131713615, compound

Product 1

HCID 131713614HCID 131713614, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of tert-butyl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxymethyl-3-cephem-4-carboxylate (syn isomer) (2.6 g) and conc. hydrochloric acid (0.9 g) in methanol (20 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was added to ethyl acetate and water, and then adjusted to pH 7.5 with a saturated aqueous sodium bicarbonate. The separated organic layer was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave tert-butyl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate (syn isomer) (2.17 g).

Workup

  1. washThe separated organic layer was washed with a saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-ac56f09bfa5f429d9427a1527b0f6df8
Source dataset
uspto-grants-1984_07
Patent number
US04462999

Reaction notes

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