N2 (benzyloxycarbonyl)-4(R)-azido-N1-tert.butyl-L-prolinamide → N2 (benzyloxycarbonyl)-4(R)-amino-N1-tert-butyl-L-prolinamide

HRID 742898Notes

Reaction equation

HRID 742898 reaction equation
N#N.[CH2:3]([O:10][C:11]([C@@:13]1([C:25]([NH2:27])=[O:26])[CH2:17][C@@H:16]([N:18]=[N+:19]=[N-])[CH2:15][N:14]1[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[N:18]#[N:19].[CH2:3]([O:10][C:11]([C@@:13]1([C:25]([NH2:27])=[O:26])[CH2:17][C@@H:16]([NH2:18])[CH2:15][N:14]1[C:21]([CH3:23])([CH3:24])[CH3:22])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 86746282N2 (benzyloxycarbonyl)-4(R)-azido-N1-tert.butyl-L-prolinamide

Product 1

HCID 86746284N2 (benzyloxycarbonyl)-4(R)-amino-N1-tert-butyl-L-prolinamideYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.345 g of N2 -(benzyloxycarbonyl)-4(R)-azido-N1 -tert.butyl-L-prolinamide was dissolved in 5 ml of dry tetrahydrofuran and the solution was evaporated. The residual gum was dissolved in 10 ml of dry tetrahydrofuran and treated under a nitrogen atmosphere with 0.262 g of triphenylphosphine. The resulting solution was left to stand under a nitrogen atmosphere at room temperature for 18 hours. 0.027 g of water was added and the solution was left to stand at room temperature for 24 hours. The solvent was then removed by evaporation and the residual gum was partitioned between water and diethyl ether. The aqueous phase was back-extracted with diethyl ether. The aqueous phase was then evaporated to give 0.09 g of N2 -(benzyloxycarbonyl)-4(R)-amino-N1 -tert.butyl-L-prolinamide as a gum. After standing overnight at room temperature the diethyl ether extracts were combined and evaporated to give 0.7 g of an oil which was chromatographed on silica gel using 10% methanol in dichloromethane for the elution to give a further 0.16 g of N2 -(benzyloxycarbonyl)-4(R)-amino-N1 -tert.butyl-L-prolinamide as a gum.

Workup

  1. customthe solution was evaporated
  2. dissolutionThe residual gum was dissolved in 10 ml of dry tetrahydrofuran
  3. additiontreated under a nitrogen atmosphere with 0.262 g of triphenylphosphine
  4. waitThe resulting solution was left
  5. addition0.027 g of water was added
  6. waitthe solution was left
  7. waitto stand at room temperature for 24 hours
  8. customThe solvent was then removed by evaporation
  9. customthe residual gum was partitioned between water and diethyl ether
  10. extractionThe aqueous phase was back-extracted with diethyl ether
  11. customThe aqueous phase was then evaporated

Sources & evidence

ORD record
ord-f28a5f549b21498090d0b1d0c7069c45
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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