Triethylamine → HCID 21948318, compound

HRID 2214832Notes

Reaction equation

HRID 2214832 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].C(N(CC)CC)C.Cl.[CH2:16]([O:18][C:19]([NH:21][C:22]1([CH2:28][N:29]2[CH2:34][CH2:33][N:32]([S:35]([C:38]3[CH:47]=[CH:46][C:45]4[C:40](=[CH:41][CH:42]=[C:43]([Cl:48])[CH:44]=4)[CH:39]=3)(=[O:37])=[O:36])[CH2:31][C:30]2=[O:49])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:20])[CH3:17]>CO>[ClH:48].[C:2]([N:25]1[CH2:26][CH2:27][C:22]([CH2:28][N:29]2[CH2:34][CH2:33][N:32]([S:35]([C:38]3[CH:47]=[CH:46][C:45]4[C:40](=[CH:41][CH:42]=[C:43]([Cl:48])[CH:44]=4)[CH:39]=3)(=[O:36])=[O:37])[CH2:31][C:30]2=[O:49])([NH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH2:23][CH2:24]1)(=[NH:7])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 21948289HCID 21948289, compound

Product 1

HCID 21948318HCID 21948318, compoundYield 162.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4N hydrochloric acid solution in ethyl acetate (30 ml) and ethanol (6 ml) were added to 1-[1-(tert-butoxycarbonyl)-4-ethoxycarbonylamino-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (5.21 g), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated, the precipitated crystals were filtered, washed with ethyl acetate-ethanol, and dried to obtain 1-[4-ethoxycarbonylamino-4-piperidinylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone hydrochloride (3.71 g). Ethyl acetimidate hydrochloride(148 mg) and triethylamine (0.337 ml) were added to a solution of 1-[4-ethoxycarbonylamino-4-piperidinylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone hydrochloride (218 mg) in methanol (10 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. After distillation of the solvent, purification by CHP20 column chromatography (water:acetonitrile:1N hydrochloric acid=100:0:0→60:40:0.5) afforded the colorless amorphous title compound (190 mg).

Workup

  1. temperaturecooling
  2. distillationAfter distillation of the solvent, purification by CHP20 column chromatography (water:acetonitrile:1N hydrochloric acid=100:0:0→60:40:0.5)

Sources & evidence

ORD record
ord-09dc196db5064497b67da7cf9e1e2515
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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