Sodium Azide → (Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

HRID 1919433Notes

Reaction equation

HRID 1919433 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6].[N-:33]=[N+:34]=[N-:35].[Na+]>CS(C)=O>[N:33]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:32])([CH3:31])[C@@H:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6])=[N+:34]=[N-:35]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131729674(Ethoxycarbonyloxy)ethyl (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86628901(Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, (ethoxycarbonyloxy)ethyl (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (37a) (4.5 g max.) dissolved in 50 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.88 g (13.5 mmol) of sodium azide (NaN3). After work-up, the crude title compound (37b) was obtained and used in the next step without further purification. The analytical data was consistent with the data obtained for (ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (32b).

Workup

  1. customAfter work-up, the crude title compound (37b) was obtained
  2. customused in the next step without further purification

Sources & evidence

ORD record
ord-77311b458f8d497da6fd6c0f30851839
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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