Hydrochloric Acid → HCID 131714996, compound

HRID 1249420Notes

Reaction equation

HRID 1249420 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:43]1[N:44]=[C:45]([NH:48]C=O)[S:46][CH:47]=1)[C:12]([NH:14][CH:15]1[C:41](=[O:42])[N:17]2[C:18]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:19](/[CH:22]=[CH:23]/[Cl:24])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.Cl.C(=O)(O)[O-].[Na+]>O.O1CCCC1>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:12]([NH:14][CH:15]1[C:41](=[O:42])[N:17]2[C:18]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])=[C:19](/[CH:22]=[CH:23]/[Cl:24])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 131714997HCID 131714997, compound

Product 1

HCID 131714996HCID 131714996, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (3.0 g) in a mixed solvent of methanol (30 ml) and tetrahydrofuran (5 ml) was added concentrated hydrochloric acid (1.67 ml) at room temperature, and the mixture was stirred for two hours at the same temperature. The reaction mixture was diluted with water (40 ml), adjusted to pH 6.0 with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and evaporated under reduced pressure. The residue was triturated with diisopropyl ether and collected by filtration to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (2.6 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-634c762893934b1881c08cda214b956e
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

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