(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoate → (S)-tert-butyl 2-amino-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoate

HRID 1775827Notes

Reaction equation

HRID 1775827 reaction equation
C(OC([NH:11][C@@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=3)=[CH:29][N:28]=2)=[CH:23][CH:22]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1>CC(=O)OCC.[Pd]>[NH2:11][C@@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=3)=[CH:31][N:32]=2)=[CH:23][CH:22]=1)[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14]

Participants

4

Reactant 1

HCID 86689673(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoate

Product 1

HCID 86689674(S)-tert-butyl 2-amino-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoate INT-10 (757 mg, 1.34 mmol) in EA (100 ml) was added Pd/C (142 mg, 0.13 mmol) and the suspension degassed with H2. The mixture was stirred vigorously under an atmosphere of H2 overnight then filtered through celite and the filtrate was concentrated to give 532 mg (88%) of (S)-tert-butyl 2-amino-3-(4-(5-(4-(tert-butyl)phenyl)pyrimidin-2-yl)phenyl)propanoate INT-11. LCMS-ESI (m/z) calculated for C27H33N3O2: 431.3. found: 432.0 [M+H]+, tR=2.01 min (Method 4).

Workup

  1. customthe suspension degassed with H2
  2. filtrationthen filtered through celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ad294f95e2894312adaaaf6d85147db4
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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