Hydrochloric Acid → HCID 131713031, compound

HRID 1195570Notes

Reaction equation

HRID 1195570 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](C=C)[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])=[CH:16][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 131713031HCID 131713031, compoundYield 97.9%

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-cephem-4carboxylic 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-aa9f8d6091e74fa7b7328d1d1f7e189b
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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