Water → HCID 21070649, compound

HRID 1435345Notes

Reaction equation

HRID 1435345 reaction equation
[CH3:1][S:2]([N:5]1[CH2:11][CH2:10][CH:9]2[CH:7]([O:8]2)[CH2:6]1)(=[O:4])=[O:3].[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C)C=O>[N:12]([CH:9]1[CH2:10][CH2:11][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH:7]1[OH:8])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 13042966HCID 13042966, compound

Product 1

HCID 21070649HCID 21070649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of rac-3-methanesulfonyl-7-oxa-3-aza-bicyclo[4.1.0]heptane (0.92 g, 5.19 mmol, Example 303) in dimethylformamide (20 mL), sodium azide (550 mg, 8.46 mmol) was added and the mixture was stirred at 80° C. for 6 hours. The mixture was cooled and poured into water and extracted with ethyl acetate (3×10 mL). The extracts were combined, washed with water, brine and dried with MgSO4. The solvent was removed to give the desired product as colorless oil. 304 mg, 30.4%. The compound was used directly for the next step.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washwashed with water, brine
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-217106aa8c144b408b45fceb683f95fe
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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