Water → HCID 59420832, compound

HRID 474013Notes

Reaction equation

HRID 474013 reaction equation
O[C:2]1([CH2:13][CH2:14][CH2:15][OH:16])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CC([O-])(C)C.[K+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C1COCC1>[C:9]([O:8][C:6]([N:4]1[CH2:3][C:2]2([O:16][CH2:15][CH2:14][CH2:13]2)[CH2:5]1)=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 59420732HCID 59420732, compound

Product 1

HCID 59420832HCID 59420832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-hydroxy-3-(3-hydroxypropyl)azetidine-1-carboxylate (27 mg, 0.13 mmol) in THF (2 ml) was added in rapid succession, KOtBu (31 mg, 0.27 mmol) and p-toluenesulfonylchloride (25 mg, 0.13 mmol) and the solution stirred at room temperature for 90 mins. Water (10 ml) was added and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to give an oil. The oil was used crude in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil

Sources & evidence

ORD record
ord-96576426befc4e1bab12afd442deddbf
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

Loading…