tert-butyl (2R,5R)-5-[(benzylamino)methyl]-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate → tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

HRID 629713Notes

Reaction equation

HRID 629713 reaction equation
C([NH:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][C@@H:13]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32](=[O:52])[C@H:33]([CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[NH:34][C:35]([O:37][CH3:38])=[O:36])[O:12][CH2:11]1)C1C=CC=CC=1.[H][H]>FC(F)(F)CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:14][C@@H:13]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32](=[O:52])[C@H:33]([CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[NH:34][C:35]([O:37][CH3:38])=[O:36])[O:12][CH2:11]1

Participants

5

Reactant 2

HCID 86726319tert-butyl (2R,5R)-5-[(benzylamino)methyl]-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86726318tert-butyl (2R,5R)-5-(aminomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a solution of tert-butyl (2R,5R)-5-[(benzylamino)methyl]-2-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate (1 eq.) in 2,2,2-trifluoroethanol (0.17M) was added Pd(OH)2 (0.33 eq.). The reaction mixture was stirred for 16 hrs under one atmosphere of hydrogen. The reaction mixture was filtered on celite and the filtrate was concentrated under reduced pressure. The residue was used as such for the next step.

Workup

  1. filtrationThe reaction mixture was filtered on celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d21f98b43fb4648a9fa9684fe56564f
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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