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

HRID 1671442Notes

Reaction equation

HRID 1671442 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:28])([CH3:27])[C@@H:11]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])(=[O:7])=[O:6].[N-:29]=[N+:30]=[N-:31].[Na+]>CS(C)=O>[N:29]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:28])([CH3:27])[C@@H:11]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])(=[O:7])=[O:6])=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866290392-Methylpropyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 866290402-Methylpropyl (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, 2-methylpropyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (30a) (0.63 g, 1.5 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.22 g (3.0 mmol) of sodium azide (NaN3). After work-up, the crude material (30b) was used in the next step without further purification. MS (ESI) m/z 463.90 (M+Na)+.

Workup

  1. customAfter work-up, the crude material (30b) was used in the next step without further purification

Sources & evidence

ORD record
ord-5391e76fd0b9420c8391db484a132e9b
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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