2,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate → 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylic acid

HRID 851601Notes

Reaction equation

HRID 851601 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[N:5]2[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[CH2:20][N:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([O:24][CH:25]([CH:27]3[CH2:29][CH2:28]3)[CH3:26])=[O:23])[C@H:4]2[S:3]1>[Zn].C(O)(=O)C>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[CH2:20][N:21]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:22]([O:24][CH:25]([CH:27]3[CH2:28][CH2:29]3)[CH3:26])=[O:23])[C@H:4]2[S:3]1

Participants

4

Reactant 1

HCID 1317112512,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate

Product 1

HCID 1317112542-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylic acidYield 87.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Zinc powder (3.0 g) was added under stirring at 5° C. to a solution of 2,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethyoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate (2.95 g) in a mixture of anhydrous dimethylformamido(12.5 ml) and acetic acid (3.75 ml), and the mixture was stirred for 1.5 hours. After the reaction, zinc powder was filtered off and washed with dimethylformamide (2 ml). The filtrate and the washings were combined, and the combined solution was extracted by pouring into a mixture of ethyl acetate (50 ml), ice-water (50 ml) and 10% hydrochloric acid (3 ml). The aqueous layer was further extracted with ethyl acetate (20 ml). The extract was combined, and then washed three times with water (20 ml) and once with a saturated sodium chloride aqueous solution and then dried over magnesium sulfate. After drying, the solvent was distilled off and the obtained residue was washed with ether and dried to give colorless crystals of 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4 -carboxylic acid (2.01 g), mp 168° to 169° C.

Workup

  1. filtrationwas filtered off
  2. washwashed with dimethylformamide (2 ml)
  3. extractionthe combined solution was extracted
  4. additionby pouring into a mixture of ethyl acetate (50 ml), ice-water (50 ml) and 10% hydrochloric acid (3 ml)
  5. extractionThe aqueous layer was further extracted with ethyl acetate (20 ml)
  6. washwashed three times with water (20 ml)
  7. dry with materialonce with a saturated sodium chloride aqueous solution and then dried over magnesium sulfate
  8. customAfter drying
  9. distillationthe solvent was distilled off
  10. washthe obtained residue was washed with ether
  11. customdried

Sources & evidence

ORD record
ord-6af3152b1e0343729a6b8f1e97e61a9c
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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