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

HRID 1441987Notes

Reaction equation

HRID 1441987 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]>[NH2:13][CH2:12][C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:24])[O:5][C:1]([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 Z8) in ethanol is hydrogenated after the addition of 20 mg of palladium on activated carbon (10%) under atmospheric pressure at RT 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-b91ff46d95fb4759b957e9607f7cf26a
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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