Benzyl {(4S)-6-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-4-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate → tert-Butyl {(1S)-4-amino-1-[2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]butyl}carbamate

HRID 269667Notes

Reaction equation

HRID 269667 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][C@H:14]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:15][C:16]([NH:18][CH2:19][C@@H:20]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:17])C1C=CC=CC=1>[Pd].C(O)C>[C:44]([O:43][C:41](=[O:42])[NH:40][C@H:14]([CH2:15][C:16]([NH:18][CH2:19][C@@H:20]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])=[O:17])[CH2:13][CH2:12][CH2:11][NH2:10])([CH3:45])([CH3:46])[CH3:47]

Participants

4

Reactant 1

HCID 86624517Benzyl {(4S)-6-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-4-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate

Product 1

HCID 86624518tert-Butyl {(1S)-4-amino-1-[2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]butyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

20 mg of palladium on activated carbon (10%) are added to a mixture of 0.127 g (0.19 mmol) of the compound from Example 230A in 10 ml of ethanol, and the mixture is then hydrogenated under atmospheric pressure for 12 h. The reaction mixture is filtered through kieselguhr, and the filtrate is concentrated in vacuo and dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through kieselguhr
  2. concentrationthe filtrate is concentrated in vacuo
  3. customdried under high vacuum
  4. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-89e3836d0b444c088124cbe3e951be22
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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