Triethylamine → HCID 67154576, compound

HRID 83059Notes

Reaction equation

HRID 83059 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([C:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH:20]=2)(O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([Cl:39])(=O)=O>ClCCl.O>[CH:1]([N:14]1[CH2:17][C:16]([C:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH:20]=2)([Cl:39])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67154497HCID 67154497, compound

Product 1

HCID 67154576HCID 67154576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-benzhydryl-3-(benzofuran-3-yl)azetidin-3-ol (760 mg, 2.14 mmol) in dichloromethane (10 mL) was added at 0° C. triethylamine (387 μL, 2.78 mmol) and then dropwise a solution of methanesulfonyl chloride (216 μL, 2.78 mmol) in dichloromethane (3 mL). The reaction mixture was stirred for 1 hour at room temperature, then diluted with water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The crude title compound was obtained as a yellow gum (873 mg, 109%) and used for the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-99f898b4185b45aaabdee714fe8b2e5d
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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