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

HRID 1780247Notes

Reaction equation

HRID 1780247 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bcf7e1412fd04ca889183090dceacfb4
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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