Water → HCID 59420832, compound

HRID 499085Notes

Reaction equation

HRID 499085 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-3b1ab2d4e56d4f10b87f450f23883a6e
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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