Hydrochloric Acid → HCID 21948289, compound

HRID 2214831Notes

Reaction equation

HRID 2214831 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][C:12]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([S:28]([C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[C:36]([Cl:41])[CH:37]=4)[CH:32]=3)(=[O:30])=[O:29])[CH2:24][C:23]2=[O:42])([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C.C(O)C>[ClH:41].[CH2:19]([O:18][C:16]([NH:15][C:12]1([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([S:28]([C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[C:36]([Cl:41])[CH:37]=4)[CH:32]=3)(=[O:29])=[O:30])[CH2:24][C:23]2=[O:42])[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1)=[O:17])[CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12071179HCID 12071179, compound

Product 1

HCID 21948289HCID 21948289, compoundYield 159%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

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. concentrationThe reaction solution was concentrated
  2. filtrationthe precipitated crystals were filtered
  3. washwashed with ethyl acetate-ethanol
  4. customdried

Sources & evidence

ORD record
ord-f75f35c6f3264ec4aa98a75ee929b8f5
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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