4-benzyl 1,4-di-tert-butyl (1S,4S)-1-[(tert-butoxycarbonyl)amino]-5-(4-nitrophenyl)-pentane-1,4,4-tricarboxylate → (5S)-2-(4-aminobenzyl)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-6-oxohexanoic acid

HRID 591335Notes

Reaction equation

HRID 591335 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:10][CH2:11][C@@:12]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:23]([O:25]CC1C=CC=CC=1)=[O:24])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:12]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[C:23]([OH:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 1317345134-benzyl 1,4-di-tert-butyl (1S,4S)-1-[(tert-butoxycarbonyl)amino]-5-(4-nitrophenyl)-pentane-1,4,4-tricarboxylate

Product 1

HCID 117777971(5S)-2-(4-aminobenzyl)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-6-oxohexanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-benzyl 1,4-di-tert-butyl (1S,4S)-1-[(tert-butoxycarbonyl)amino]-5-(4-nitrophenyl)-pentane-1,4,4-tricarboxylate (1.04 g, 1.618 mmol) were dissolved in methanol (20 ml). Palladium (10% on charcoal) (52 mg) was added and the suspension was shaken under a hydrogen atmosphere for 12 h. The catalyst was filtered off, the residue was concentrated in vacuo, and the product was obtained as white foam (864 mg, quant.).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe residue was concentrated in vacuo
  3. customthe product was obtained as white foam (864 mg, quant.)

Sources & evidence

ORD record
ord-891b3daa174b4ea0a3f540a0a5ea932f
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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