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

HRID 1671434Notes

Reaction equation

HRID 1671434 reaction equation
Cl[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][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[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][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:13])(=[O:7])=[O:6])=[N+:34]=[N-:35]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866290272-Morpholin-4-ylethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 866290282-Morpholin-4-ylethyl (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-morpholin-4-ylethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (26a) (0.41 g, 0.83 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 0.12 g (1.7 mmol) of sodium azide (NaN3). After work-up, the crude material (26b) was used in the next step without further purification. MS (ESI) m/z 499.12 (M+H)+.

Workup

  1. customAfter work-up, the crude material (26b) was used in the next step without further purification

Sources & evidence

ORD record
ord-374ce1504cc0419888e12ab5bcc864b6
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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