Sodium Azide → HCID 86629043, compound

HRID 1671445Notes

Reaction equation

HRID 1671445 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:7])=[O:6].[N-:34]=[N+:35]=[N-:36].[Na+]>CS(C)=O>[N:34]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:7])=[O:6])=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86629042HCID 86629042, compound

Product 1

HCID 86629043HCID 86629043, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, phenylmethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoate (31a) (0.44 g, 0.9 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 81 mg (1.1 mmol) of sodium azide (NaN3). After work-up, the crude title compound (31b) was purified by silica gel column chromatography and used in the next step. Rf=0.59 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3): δ=1.02 (s, 6H), 1.98-2.10 (m, 2H), 3.07-3.13 (m, 2H), 3.63-3.65 (m, 2H), 3.81 (s, 3H), 3.85 (s, 1H), 3.94 (d, J=9.2 Hz, 1H), 4.18 (d, J=9.2 Hz, 1H), 4.27 (d, J=11.2 Hz, 1H), 4.53 (d, J=10.8 Hz, 1H), 5.20 (s, 2H), 6.85 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 7.37-7.39 (m, 5H) ppm. MS (ESI) m/z 528.15 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up, the crude title compound (31b) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c1b95c563ff43f5a5150ac17bc5294d
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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