Sodium Azide → HCID 86628918, compound

HRID 1919450Notes

Reaction equation

HRID 1919450 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:41])([CH3:40])[C@@H:11]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18](=[O:31])[C:19]([CH3:30])([CH3:29])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:13])(=[O:7])=[O:6].[N-:42]=[N+:43]=[N-:44].[Na+]>CS(C)=O>[N:42]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:41])([CH3:40])[C@@H:11]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18](=[O:31])[C:19]([CH3:30])([CH3:29])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:13])(=[O:7])=[O:6])=[N+:43]=[N-:44]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86628919HCID 86628919, compound

Product 1

HCID 86628918HCID 86628918, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, [2,2-dimethyl-3-(phenylmethoxy)propanoyloxy]ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (46a) (0.47 g, 0.77 mmol, max.) dissolved in 4 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 90 mg (1.4 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 n-heptane (Hptn) (EtOAc/Hptn=1:4) as eluent to provide a mixture of 0.13 g (27% yield) of the title compound (46b). Rf=0.17 (EtOAc/Hept=1:4). MS (ESI) m/z 642.20 (M+Na)+.

Workup

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

Sources & evidence

ORD record
ord-38a7550352684c2bbf853b4b190a7c40
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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