Hydrochloric Acid → HCID 131713212, compound

HRID 569427Notes

Reaction equation

HRID 569427 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:26]2[N:27]=[C:28]([NH:31]C=O)[S:29][CH:30]=2)[C:9]([NH:11][CH:12]2[C:24](=[O:25])[N:14]3[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH:19]=[CH2:20])[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl.O.C(=O)(O)[O-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[CH:1]1([O:6][N:7]=[C:8]([C:26]2[N:27]=[C:28]([NH2:31])[S:29][CH:30]=2)[C:9]([NH:11][CH:12]2[C:24](=[O:25])[N:14]3[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH:19]=[CH2:20])[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 516892Sodium BicarbonateHCID 131713213HCID 131713213, compound

Product 1

HCID 131713212HCID 131713212, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-[2-(2-cyclopenten-1-yloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (3.1 g) in methanol (22 ml), tetrahydrofuran (10 ml) and conc. hydrochloric acid (1.3 g) was stirred for 2.5 hours at ambient temperature. The reaction mixture was added to a mixture of water and ethyl acetate, and adjusted to pH 7.5 with a saturated aqueous sodium bicarbonate. The separated aqueous layer was adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were filtered off, washed with water and dried over phosphorus pentoxide in vacuo to give 7-[2-(2-cyclopenten-1-yloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (2.7 g).

Workup

  1. filtrationThe precipitates were filtered off
  2. washwashed with water
  3. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-4e8134e59f374e3eb9a5c76cf899ac6b
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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