Water → HCID 57868875, compound

HRID 1966132Notes

Reaction equation

HRID 1966132 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.C(N(CC)C(C)C)(C)C.[CH:16]1([S:19](Cl)(=[O:21])=[O:20])[CH2:18][CH2:17]1.O>O1CCCC1>[CH:16]1([S:19]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)(=[O:21])=[O:20])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 2760919Cyclopropanesulfonyl chloride

Product 1

HCID 57868875HCID 57868875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of azetidin-3-ol hydrochloride (1.00 g, 9.13 mmol) (purchased from Matrix) and N,N-diisopropylethylamine (4.77 mL, 27.4 mmol) in tetrahydrofuran (100 mL) at 0° C. was added cyclopropanesulfonyl chloride (0.930 mL, 9.13 mmol) and the reaction was stirred for 16 hours. Water was added and the product was extracted with ethyl acetate. The combined extracts were washed with 1N HCl, saturated sodium bicarbonate, and brine, dried over sodium sulfate, decanted and concentrated to afford a yellow oil used without further purification (1.04 g, 64%). 1H NMR (300 MHz, CDCl3): 4.61 (p, 1H), 4.14-4.07 (m, 2H), 3.93-3.86 (m, 2H), 2.69 (br s, 1H), 2.42-2.32 (m, 1H), 1.20-1.11 (m, 2H), 1.06-0.98 (m, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined extracts were washed with 1N HCl, saturated sodium bicarbonate, and brine
  3. dry with materialdried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. customto afford a yellow oil
  7. customused without further purification (1.04 g, 64%)

Sources & evidence

ORD record
ord-2408e9c794ce487ebb28c43d58db0f3d
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

Loading…