O-Methylhydroxylamine hydrochloride → HCID 131710493, compound

HRID 972487Notes

Reaction equation

HRID 972487 reaction equation
[CH:1]([C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:12](=[O:23])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])=O.Cl.[CH3:25][O:26][NH2:27]>O1CCCC1.O>[CH3:25][O:26][N:27]=[CH:1][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:12](=[O:23])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 88819529HCID 88819529, compound

Product 1

HCID 131710493HCID 131710493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-formyl-7β-(2-thienylacetamido)-3-cephem-4-carboxylic acid (35 mg) in tetrahydrofuran (3 ml) is added a solution of O-methylhydroxylamine hydrochloride (13 mg) in water (1.5 ml), and the mixture is left standing for 24 hours. After evaporation of the tetrahydrofuran at room temperature, the separated yellow oil is extracted with ethyl acetate. The extract solution is washed with water, dried and evaporated to leave pale yellow foam which gives crystals of 3-methoxyiminomethyl-7β-(2-thienylacetamido)-3-cephem-4-carboxylic acid (37 mg; nearly quantitative yield) by recrystallization from ether and ethyl acetate. m.p. 186°-189° C.

Workup

  1. waitthe mixture is left
  2. customAfter evaporation of the tetrahydrofuran at room temperature
  3. extractionthe separated yellow oil is extracted with ethyl acetate
  4. washThe extract solution is washed with water
  5. customdried
  6. customevaporated
  7. customto leave pale yellow foam which

Sources & evidence

ORD record
ord-2540aea182704a018bec6cb7ca7ef04e
Source dataset
uspto-grants-1977_10
Patent number
US04053469

Reaction notes

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