tert-butyl-{(4S)-5-azido-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate → tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

HRID 269614Notes

Reaction equation

HRID 269614 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][N:13]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][NH2:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86612278tert-butyl-{(4S)-5-azido-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Product 1

HCID 57440197tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 188 mg (0.55 mmol) of tert-butyl{(4S)-5-azido-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 85A) in ethanol is hydrogenated after the addition of 20 mg of palladium on activated carbon (10%) at RT under atmospheric pressure for 12 h. The mixture is filtered through kieselguhr, and the residue is washed with ethanol. The filtrate is evaporated to dryness in vacuo. The product is reacted without further purification.

Workup

  1. filtrationThe mixture is filtered through kieselguhr
  2. washthe residue is washed with ethanol
  3. customThe filtrate is evaporated to dryness in vacuo
  4. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-5c7c2cd4bb7847fea456a2d6852b2add
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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