Sodium Azide → HCID 57300086, compound

HRID 1740476Notes

Reaction equation

HRID 1740476 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][C@@H:9]1[CH2:24][O:25][C:26]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:49]=[N+:50]=[N-:51].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:49]=[N+:50]=[N-:51])[CH2:10][C@@H:9]1[CH2:24][O:25][C:26]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 54480540HCID 54480540, compound

Product 1

HCID 57300086HCID 57300086, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(2R,4R)-1-(tert-Butyloxycarbonyl)-2-(4,4'-Dimethoxytrityl)oxymethyl-4-[(p-toluenesulfonyl)oxy]pyrrolidine 39 (5.1 g, 7.58 mmol) was dissolved in dimethylformamide (50 ml) and diluted with water (5 ml ). To this stirred solution was added sodium azide (0.65 g, 10 mmol) and heated at 80° C. for 8 h. It was cooled and evaporated to dryness. The residue was partitioned between CH2Cl2 (200 ml) and water (100 ml), and extracted in CH2Cl2. The organic extract was washed with brine (50 ml), dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The pure fractions were pooled together and evaporated to give 3.8 g (92%) of a clear oil. 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 3.74 (s, 6H, 2.0CH3), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 6.82 (d, 4H, Ph), and 7.26-7.80 (m, 9H, Ph).

Workup

  1. temperatureIt was cooled
  2. customevaporated to dryness
  3. customThe residue was partitioned between CH2Cl2 (200 ml) and water (100 ml)
  4. extractionextracted in CH2Cl2
  5. extractionThe organic extract
  6. washwas washed with brine (50 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe crude product was purified by flash chromatography over silica gel
  10. customevaporated

Sources & evidence

ORD record
ord-18ca873b27a74843aa87c2882610be59
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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