Triethylamine → HCID 131714355, compound

HRID 980979Notes

Reaction equation

HRID 980979 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:40][O:41][CH3:42])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24][CH:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])=[C:17]([CH:20]=[O:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:40][O:41][CH3:42])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[CH:16]([C:22]([O:24][CH:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[C:17]([CH:20]=[O:21])=[CH:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 131714353HCID 131714353, compound

Product 1

HCID 131714355HCID 131714355, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-formyl-3-cephem-4-carboxylate (syn isomer) (3 g) and triethylamine (0.45 g) in tetrahydrofuran (30 ml) was stirred at ambient temperature for 40 minutes. To the reaction mixture was added ethyl acetate (50 ml) and washed with 3% hydrochloric acid and brine. The organic solution was dried over magnesium sulfate and evaporated. The residue was pulverized in diisopropyl ether to give benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-formyl-2-cephem-4-carboxylate (syn isomer) (2.48 g).

Workup

  1. washwashed with 3% hydrochloric acid and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-00933c3c854d4fb2ac2cd2b5d4a2efc1
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

Loading…