Hydrochloric Acid → 1-{(2S,3S)-3-[N2-(4-Aminophenoxyacetyl)-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride

HRID 1780247노트

반응식

HRID 1780247 반응식
[ClH:1].C(OC([NH:12][C:13]1[CH:55]=[CH:54][C:16]([O:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@@H:30]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:31]([OH:46])[C:32]([N:34]2[CH2:45][CH2:44][CH2:43][C@H:35]2[C:36]([NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:33])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1>CO.[Pd]>[ClH:1].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@@H:30]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:31]([OH:46])[C:32]([N:34]2[CH2:45][CH2:44][CH2:43][C@H:35]2[C:36]([NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:33])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:54][CH:55]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 700489921-[(2S,3S)-3-{N2-[4-(Benzyloxycarbonylamino)phenoxyacetyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide

생성물 1

HCID 867508191-{(2S,3S)-3-[N2-(4-Aminophenoxyacetyl)-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride수율 98.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

0.16 ml (0.16 mmol) of 1N aqueous hydrochloric acid was added to a solution of 105 mg (0.14 mmol) of 1-[(2S,3S)-3-{N2 -[4-(benzyloxycarbonylamino)phenoxyacetyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide (prepared as described in Example 16) in 5 ml of methanol, and the mixture was stirred for 2.5 hours in the presence of 70 mg of palladium on charcoal and under an atmosphere of hydrogen. At the end of this time, the catalyst was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with benzene and the mixture was dehydrated by azeotropic distillation. This operation was repeated a second time, and then the residue was triturated with diethyl ether, to give 89 mg of the title compound as a red-brown powder, melting at 165°-168° C.

후처리

  1. customAt the end of this time, the catalyst was removed by filtration
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionThe resulting residue was mixed with benzene
  4. distillationthe mixture was dehydrated by azeotropic distillation
  5. customthe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-bcf7e1412fd04ca889183090dceacfb4
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629406

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