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

HRID 1671431Notes

Reaction equation

HRID 1671431 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:27])([CH3:26])[C@@H:11]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])(=[O:7])=[O:6].[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O>[N:28]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:27])([CH3:26])[C@@H:11]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])(=[O:7])=[O:6])=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86629024Isopropyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86629025Isopropyl (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, isopropyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (25a) (0.61 g, 1.4 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.21 g (2.9 mmol) of sodium azide (NaN3). After work-up, the crude material (25b) was used in the next step without further purification or isolation. MS (ESI) m/z 450.13 (M+Na)+.

Workup

  1. customAfter work-up, the crude material (25b) was used in the next step without further purification or isolation

Sources & evidence

ORD record
ord-3ab810eee3ec443d889da28335de4c47
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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