Water → HCID 68132614, compound

HRID 1605401Notes

Reaction equation

HRID 1605401 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH:10]([O:23][C:24]([CH:26]1[N:31]2[C:32](=[O:43])[CH:33]([NH:34][C:35](=[O:42])[CH2:36][C:37]3[S:38][CH:39]=[CH:40][CH:41]=3)[C@H:30]2[S:29][CH:28]=[C:27]1[CH2:44]O)=[O:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(Cl)Cl>[F:7][CH2:44][C:27]1[CH:26]([C:24]([O:23][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:25])[N:31]2[C:32](=[O:43])[CH:33]([NH:34][C:35](=[O:42])[CH2:36][C:37]3[S:38][CH:39]=[CH:40][CH:41]=3)[C@H:30]2[S:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 68131874Benzhydryl 7-(2-thienylacetamido)-3-hydroxymethyl-2-cephem-4-carboxylate

Product 1

HCID 68132614HCID 68132614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.322 g of diethylaminosulfur trifluoride in 10 ml of CH2Cl2 at -78° under N2 is added a solution of 1.04 g of benzhydryl-3-hydroxymethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylate in 50 ml of CH2Cl2. The mixture is stirred for 0.5 hour then poured into 100 ml of H2O and the CH2Cl2 layer dried (MgSO4) and evaporated in vacuo. The residue is chromatographed on silica with CHCl3 to give benzhydryl 3-fluoromethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylate, which can be purified by recrystallization from methanol.

Workup

  1. dry with materialthe CH2Cl2 layer dried (MgSO4)
  2. customevaporated in vacuo
  3. customThe residue is chromatographed on silica with CHCl3

Sources & evidence

ORD record
ord-a2a1b66cda764424a89cc7bc656aa3db
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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