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

HRID 54110Notes

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

Participants

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

customThe mixture was evaporated under an oil pump vacuum
customto give a solid which
customwas partitioned between ethyl acetate and water
washThe ethyl acetate phase was washed with saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulphate
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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