Sodium Azide → HCID 131729105, compound

HRID 1671448Notes

Reaction equation

HRID 1671448 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:24])([CH3:23])[CH:11]([OH:22])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:7])=[O:6].[N-:25]=[N+:26]=[N-:27].[Na+]>CS(C)=O>[N:25]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:24])([CH3:23])[CH:11]([OH:22])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:7])=[O:6])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131729104HCID 131729104, compound

Product 1

HCID 131729105HCID 131729105, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, phenylmethyl (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-hydroxybutanoate (32b) (0.10 g, 0.26 mmol) dissolved in 3 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 43 mg (0.66 mmol) of sodium azide (NaN3). After work-up, the crude title compound (32c) was used in the next step without further purification. MS (ESI) m/z 407.96 (M+Na)+.

Workup

  1. customAfter work-up, the crude title compound (32c) was used in the next step without further purification

Sources & evidence

ORD record
ord-53e60fb1eedb419e9147146cd2e028b7
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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