Triethylamine → 7-Cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid Benzhydryl Ester

HRID 1287604Notes

Reaction equation

HRID 1287604 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]([O:25][C:26]([C:28]1[N:33]2[C:34](=[O:37])[CH:35]([NH2:36])[C@H:32]2[S:31][CH2:30][C:29]=1[OH:38])=[O:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:39]([CH2:41][CH2:42][C:43](Cl)=[S:44])#[N:40].C(N(CC)CC)C>C(Cl)Cl>[CH:12]([O:25][C:26]([C:28]1[N:33]2[C:34](=[O:37])[CH:35]([NH:36][C:43](=[S:44])[CH2:42][CH2:41][C:39]#[N:40])[C@H:32]2[S:31][CH2:30][C:29]=1[OH:38])=[O:27])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19989189Cyanomethylthioacetyl chlorideHCID 1317104817-Amino-3-cephem-3ol-4-carboxylic acid benzhydryl ester p-toluenesulfonate salt

Product 1

HCID 1317104807-Cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid Benzhydryl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

7-Amino-3-cephem-3ol-4-carboxylic acid benzhydryl ester p-toluenesulfonate salt [Helv. Chim. Acta 57, 1919 (1974)], (242 mg.) is dissolved in methylene chloride (5 ml.), cooled in an ice bath, and cyanomethylthioacetyl chloride (68 mg.) in methylene chloride (3 ml.) is added, followed by 125 μl of triethylamine. The mixture is stirred for 3.5 hours at 0°-5° and then is allowed to stand overnight in the refrigerator. After diluting with methylene chloride, the reaction mixture is washed with water, then with pH 4 buffer, and dried (Na2SO4). Solvent is removed in vacuo yielding the desired product as a oil (204 mg.); NMR (CDCl3, δ) 3.33 (m,CH2), 3.45 (s, NCCH2SCH2 --) 5.05 (d, J=4.5 Hz, H6), 5.65 (q. J=4.5, 9Hz, H7), 6.93 (s,CHφ2), 7.33 (s, aromatic H's), 7.80 (d, J=9Hz, NH); νmax (CH2Cl2) 3380, 3310, 2225, 1785, 1735, 1690 cm-1.

Workup

  1. temperaturecooled in an ice bath
  2. waitto stand overnight in the refrigerator
  3. washthe reaction mixture is washed with water
  4. dry with materialwith pH 4 buffer, and dried (Na2SO4)
  5. customSolvent is removed in vacuo

Sources & evidence

ORD record
ord-35905fcb6923470d8202d30517dcac83
Source dataset
uspto-grants-1976_10
Patent number
US03985746

Reaction notes

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