Sodium Azide → HCID 53641990, compound

HRID 399527Notes

Reaction equation

HRID 399527 reaction equation
[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@@H:10]([N:25]=[N+:26]=[N-:27])[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 71740081HCID 71740081, compound

Product 1

HCID 53641990HCID 53641990, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of (4S)-1-(tert-butyloxycarbonyl)-4-(methanesulfonyloxy)-L-proline tert-butyl ester (250 mg, 0.684 mmol) and sodium azide (222 mg, 3.42 mmol) in N,N-dimethylformamide (1.5 mL) was stirred for 18 hours at 55° C. under a nitrogen atmosphere. The cooled reaction mixture was evaporated and partitioned between diluted ethyl acetate and water. The organic layer was washed with water, 0.1N hydrochloric acid, water, saturated brine solution, dried (Na2SO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting with 10% ethyl acetate/hexane. The desired azide was obtained as a colorless oil; yield 196 mg (92%). 400 MHz 1H NMR (CDCl3): δ1.42-1.45 (3s, 18H); 2.11 (m, 1H); 2.22-2.36 (m, 1H); 3.68 (m, 1H); 4.12 (m, 1H).

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated
  3. custompartitioned between diluted ethyl acetate and water
  4. washThe organic layer was washed with water, 0.1N hydrochloric acid, water, saturated brine solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-23bdf69bf7ec462fbd2f0649f1aadae7
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

Loading…