Triethylamine → 7-Cyanomethylthioacetamido-3-cephem-4-carboxylic acid benzhydryl ester

HRID 1287610Notes

Reaction equation

HRID 1287610 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:26])[CH:24]([NH2:25])[C@H:21]2[S:20][CH2:19][CH:18]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([CH2:29][CH2:30][C:31](Cl)=[S:32])#[N:28].C(N(CC)CC)C>C(Cl)Cl>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:26])[CH:24]([NH:25][C:31](=[S:32])[CH2:30][CH2:29][C:27]#[N:28])[C@H:21]2[S:20][CH2:19][CH:18]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylateHCID 19989189Cyanomethylthioacetyl chloride

Product 1

HCID 1317104887-Cyanomethylthioacetamido-3-cephem-4-carboxylic acid benzhydryl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

7-Amino-3-cephem-4-carboxylic acid benzhydryl ester (366 mg.) (prepared by the method of Netherlands Patent no. 7,309,135) is dissolved in methylene chloride (5 ml.), cooled in an ice bath, and cyanomethylthioacetyl chloride (149 mg.) in methylene chloride (5 ml.) is added followed by triethylamine (101 mg.). The mixture is stirred for 4 hours at 0°-5° and, after diluting with methylene chloride the reaction mixture is washed with water then with pH 4 buffer, and dried (Na2SO4). The solvent is removed in vacuo yielding the product 7-cyanomethylthioacetamido-3-cephem-4-carboxylic acid benzhydryl ester as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. washis washed with water
  3. dry with materialwith pH 4 buffer, and dried (Na2SO4)
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6e16143f7a494e50abacbdae8dc5830f
Source dataset
uspto-grants-1976_10
Patent number
US03985746

Reaction notes

Loading…