Water → HCID 86732632, compound

HRID 626393Notes

Reaction equation

HRID 626393 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C@H:14]2[CH2:17][CH2:16][O:15]2)(=O)=O)=CC=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CS(C)=O>[N:18]([CH2:12][CH2:13][C@H:14]1[CH2:17][CH2:16][O:15]1)=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86732633HCID 86732633, compound

Product 1

HCID 86732632HCID 86732632, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

The mixture of (R)-2-(oxetan-2-yl)ethyl 4-methylbenzenesulfonate (80 mg, 0.31 mmol), NaN3 (30 m2, 0.465 mmol) and KI (5 mg) in DMSO (1 mL) was heated to 55° C. and stirred for 18 h. Then the mixture was cooled to RT, then it was poured into 20 mL of water, then extracted with MTBE (20 mL×3), the organic layers was washed with 1-120 (10 mL), brine (10 mL), and dried over Na2SO4. After filtration, the filtrate was concentrated under the reduced pressure. to give the titled compound which was used to the next step without further purification.

Workup

  1. temperatureThen the mixture was cooled to RT
  2. extractionextracted with MTBE (20 mL×3)
  3. washthe organic layers was washed with 1-120 (10 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-3cd014bad5fc4d2fa9dc946c3275d6de
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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