Dimethyl Sulfoxide → HCID 59786104, compound

HRID 2410370Notes

Reaction equation

HRID 2410370 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[O:17][C:18]1[C:23]2[C:24]([O:27][CH2:28][CH:29]3[CH2:34][CH2:33][N:32]([CH2:35][C:36]4([OH:42])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH2:31][CH2:30]3)=[N:25][O:26][C:22]=2[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl.O>[OH:42][C:36]1([CH2:35][N:32]2[CH2:33][CH2:34][CH:29]([CH2:28][O:27][C:24]3[C:23]4[C:18]([O:17][CH:13]5[CH2:14][CH2:15][CH2:16][C:12]5=[O:11])=[CH:19][CH:20]=[CH:21][C:22]=4[O:26][N:25]=3)[CH2:30][CH2:31]2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53357014HCID 53357014, compound

Product 1

HCID 59786104HCID 59786104, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (9 μL, 0.1 mmol) in dichloromethane (0.5 mL) was added dimethylsulfoxide (9 μM, 0.12 mmol) at −78° C. under nitrogen. The mixture was stirred for 5 min, a solution of 4-({4-[({4-[(trans-2-Hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]-piperidin-1-yl}methyl)tetrahydro-2H-pyran-4-ol (EXAMPLE 32) in dichloromethane (1.5 mL) was added to the mixture. After being stirred for 5 min, triethylamine (45 μL, 0.33 mmol) was added to the mixture. The mixture was allowed to warmed to room temperature and stirred for 3 h. Water was added to the mixture and the mixture was extracted with ethyl acetate and washed with brine. The extract was dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (dichloromethane/methanol 20:1) to give 13 mg (45%) of the title compound as a white solid.

Workup

  1. stirringAfter being stirred for 5 min
  2. stirringstirred for 3 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe residual oil was purified by silica gel column chromatography (dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-8185e765a44e4173a6111cef66aec65d
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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