benzyl{(1S)-3-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]propyl}carbamate → Tert-butyl[3-({(2s)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoyl}amino)-2-hydroxypropyl]carbamate

HRID 269625Notes

Reaction equation

HRID 269625 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:22]([NH:24][CH2:25][CH:26]([OH:36])[CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:23])[CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])C1C=CC=CC=1>CO.[Pd]>[C:32]([O:31][C:29](=[O:30])[NH:28][CH2:27][CH:26]([OH:36])[CH2:25][NH:24][C:22](=[O:23])[C@@H:11]([NH2:10])[CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])([CH3:33])([CH3:34])[CH3:35]

Participants

4

Reactant 1

HCID 131727150benzyl{(1S)-3-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]propyl}carbamate

Product 1

HCID 89225963Tert-butyl[3-({(2s)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoyl}amino)-2-hydroxypropyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

38 mg (0.12 mmol) of the compound from Example 98A are dissolved in 10 ml of methanol, and 10 mg of palladium on activated carbon (10%) are added. The mixture is hydrogenated under atmospheric pressure for 2 h and filtered through kieselguhr, and the mother liquor is concentrated in vacuo.

Workup

  1. filtrationfiltered through kieselguhr
  2. concentrationthe mother liquor is concentrated in vacuo

Sources & evidence

ORD record
ord-2ca48361dea845028d87750143e1add3
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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