O-Methylhydroxylamine hydrochloride → HCID 131710493, compound

HRID 1287989Notes

Reaction equation

HRID 1287989 reaction equation
CO[CH:3](OC)[C:4]1[CH2:5][S:6][C@@H:7]2[C@H:14]([NH:15][C:16](=[O:23])[CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:13](=[O:24])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11].Cl.[CH3:28][O:29][NH2:30]>O1CCCC1.O>[CH3:28][O:29][N:30]=[CH:3][C:4]1[CH2:5][S:6][C@@H:7]2[C@H:14]([NH:15][C:16](=[O:23])[CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:13](=[O:24])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 70636652HCID 70636652, compound

Product 1

HCID 131710493HCID 131710493, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-dimethoxymethyl-7β-(2-thienylacetamido)-3-cephem-4-carboxylic acid (76 mg) in tetrahydrofuran (4 ml) is added a solution of O-methylhydroxylamine hydrochloride (23 mg) in water (1 ml), and the mixture is kept at room temperature for 10 hours. The reaction mixture is evaporated to remove tetrahydrofuran, and the separated solid material is collected by filtration. Recrystallization of the solid from a mixture of ethyl acetate and ether gives 3-methoxyiminomethyl-7β-(2-thienylacetamido)-3-cephem-4-carboxylic acid (61 mg). m.p. 186°-189° C. Yield: 80%.

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove tetrahydrofuran
  3. filtrationthe separated solid material is collected by filtration
  4. customRecrystallization of the solid
  5. additionfrom a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-d3ff20c9b38446bca9e93a280b1aacd8
Source dataset
uspto-grants-1976_10
Patent number
US03987039

Reaction notes

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