Sodium Azide → HCID 86628915, compound

HRID 1919446Notes

Reaction equation

HRID 1919446 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:35])([CH3:34])[C@@H:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])=[O:13])(=[O:7])=[O:6].[N-:36]=[N+:37]=[N-:38].[Na+]>CS(C)=O>[N:36]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:35])([CH3:34])[C@@H:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])=[O:13])(=[O:7])=[O:6])=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86628914HCID 86628914, compound

Product 1

HCID 86628915HCID 86628915, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, (cyclohexylcarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (44a) (1.6 g, 3.0 mmol) dissolved in 15 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.65 g (10.0 mmol) of sodium azide (NaN3). After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:4) as eluent to provide 1.1 g (65% yield) of the title compound (44b) as a colorless oil. Rf=0.30 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.04-1.06 (m, 6H), 1.19-1.30 (br. m, 3H), 1.40-1.49 (br. m, 2H), 1.51 (d, J=5.6 Hz, 3H), 1.62-1.66 (br. m, 1H), 1.70-1.78 (br. m, 2H), 1.85-1.94 (br. m, 2H), 2.01-2.08 (m, 2H), 2.24-2.37 (m, 1H), 3.09-3.15 (m, 2H), 3.43-3.47 (m, 2H), 3.81-3.83 (2s, 1H), 3.93 (d, J=8.8 Hz, 1H), 4.17-4.22 (m, 1H), 4.32-4.36 (2d, J=11.6, 11.2 Hz, 1H), 4.56-4.65 (2d, J=11.6, 11.6 Hz, 1H), 6.91-6.95 (m, 1H), 7.32-7.37 (m, 5H) ppm. MS (ESI) m/z 562.13 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up, the crude material was purified by silica gel column chromatography
  2. additiona mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:4) as eluent

Sources & evidence

ORD record
ord-baeb8da4aeb0435990fe8c4107bda0cb
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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