Sodium Azide → HCID 86628912, compound

HRID 1919443Notes

Reaction equation

HRID 1919443 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:36])([CH3:35])[C@@H:11]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:19])=[O:13])(=[O:7])=[O:6].[N-:37]=[N+:38]=[N-:39].[Na+]>CS(C)=O>[N:37]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:36])([CH3:35])[C@@H:11]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:19])=[O:13])(=[O:7])=[O:6])=[N+:38]=[N-:39]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86628911HCID 86628911, compound

Product 1

HCID 86628912HCID 86628912, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, 0.4 g (0.73 mmol) of (cyclohexyloxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (43a) dissolved in 4 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.16 g (2.5 mmol) of sodium azide (NaN3). After work-up, 0.35 g (85% yield) of the title compound (43b) was obtained as a colorless oil. Rf=0.35 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.06-1.08 (m, 6H), 1.25-1.58 (br. m, 9H), 1.72-1.78 (br. m, 2H), 1.88-1.96 (br. m, 2H), 2.03-2.10 (m, 2H), 3.10-3.16 (m, 2H), 3.44-3.48 (m, 2H), 3.84-3.85 (2s, 1H), 3.94-3.96 (2d, J=9.2, 8.8 Hz, 1H), 4.18-4.23 (2d, J=9.2, 9.2 Hz, 1H), 4.33-4.38 (2d, J=11.2 Hz, 11.6 Hz, 1H), 4.54-4.72 (m, 2H), 6.81-6.87 (m, 1H), 7.30-7.38 (m, 5H) ppm. MS (ESI) m/z 577.89 (M+Na)+. The analytical data was consistent with the proposed structure.

Sources & evidence

ORD record
ord-829da83b2b0c4982b324fdcdf590cf7f
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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