Water → HCID 59420847, compound

HRID 474008Notes

Reaction equation

HRID 474008 reaction equation
O[C:2]1([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[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[CH2:5][C:2]2([O:15][CH2:14][C:13]2([CH3:17])[CH3:16])[CH2:3]1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 594207111,1-Dimethylethyl 3-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)-1-azetidinecarboxylate

Product 1

HCID 59420847HCID 59420847, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-hydroxy-3-(1-hydroxy-2-methylpropan-2-yl)azetidine-1-carboxylate (0.20 g, 0.82 mmol) in THF (4 ml) was added in rapid succession, KOtBu (0.19 g, 1.72 mmol) and p-toluenesulfonylchloride (0.16 g, 0.82 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 purified by flash column chromatography eluting with 30 to 70% ethylacetate/hexanes to give the title compound as a colorless oil 0.13 g, 70%. 1H NMR (CDCl3, 400 Mhz) 1.25 (6H, s), 1.45 (9H, s), 3.89 (2H, d), 4.12 (2H, d), 4.20 (2H, s).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil
  5. customThe oil was purified by flash column chromatography
  6. washeluting with 30 to 70% ethylacetate/hexanes

Sources & evidence

ORD record
ord-90f044caf8874f22b9ab387027aa7468
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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