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

HRID 54110
Notes
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Reaction equation

HRID 54110 reaction equation
N#N.[CH2:3]([O:10][C:11]([C@@:13]1([C:27]([NH2:29])=[O:28])[CH2:17][C@H:16](OS(C)(=O)=O)[CH2:15][N:14]1[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[N:30]#[N:31].[CH2:3]([O:10][C:11]([C@@:13]1([C:27]([NH2:29])=[O:28])[CH2:17][C@@H:16]([N:30]=[N+:31]=[N-:32])[CH2:15][N:14]1[C:23]([CH3:24])([CH3:26])[CH3:25])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86746278N2 (benzyloxycarbonyl)-N1-tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide

Product 1

HCID 86746282N2 (benzyloxycarbonyl)-4(R)-azido-N1-tert.butyl-L-prolinamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

0.5 g of N2 -(benzyloxycarbonyl)-N1 -tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide was dissolved in 10 ml of dry dimethylformamide and treated with 0.330 g of sodium azide. The heterogeneous mixture was stirred and heated at 75° C. for 18 hours. The mixture was evaporated under an oil pump vacuum to give a solid which was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. The solvent was removed by evaporation to give 0.345 g of N2 -(benzyloxycarbonyl)-4(R)-azido-N1 -tert.butyl-L-prolinamide in the form of a gum.

Workup

  1. customThe mixture was evaporated under an oil pump vacuum
  2. customto give a solid which
  3. customwas partitioned between ethyl acetate and water
  4. washThe ethyl acetate phase was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-8fcf24b3d1ea409290be4e22b0fe4762
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05620987

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes