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

HRID 1671438Notes

Reaction equation

HRID 1671438 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:29])([CH3:28])[C@@H:11]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[O:13])(=[O:7])=[O:6].[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O>[N:30]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:29])([CH3:28])[C@@H:11]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[O:13])(=[O:7])=[O:6])=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866290322-(Dimethylamino)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 866290332-(Dimethylamino)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, 2-(dimethylamino)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (28a) (0.70 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 (28b) was used in the next step without further purification. MS (ESI) m/z 456.90 (M+H)+.

Workup

  1. customAfter work-up, the crude material (28b) was used in the next step without further purification

Sources & evidence

ORD record
ord-c21c15a884d444999278de63104bcaa3
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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