Methanesulfonyl chloride → HCID 90133853, compound

HRID 1051389Notes

Reaction equation

HRID 1051389 reaction equation
[F:1][C:2]([F:24])([F:23])[CH:3]([CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:8]1)[CH2:4][OH:5].CCN(C(C)C)C(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[CH:3]([CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[CH2:8]1)[CH2:4][O:5][S:35]([CH3:34])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118323818HCID 118323818, compound

Product 1

HCID 90133853HCID 90133853, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 50 mL round-bottomed flask, 3,3,3-trifluoro-2-((2-(3-(trifluoromethyl)phenyl)morpholino)-methyl)propan-1-ol (760 mg, 2.13 mmol) was combined with CH2Cl2 (10.0 ml) to give a colorless solution and then cooled to 0° C. DIPEA (412 mg, 557 μl, 3.19 mmol) and methanesulfonyl chloride (244 mg, 166 μl, 2.13 mmol) were added dropwise and the resulting reaction mixture was stirred for 30 min. The reaction was diluted with CH2Cl2 (30 ml), washed with sat. NaHCO3 solution followed by washing with H2O, dried over MgSO4, filtered and concentrated to give 880 mg (95%) of methanesulfonic acid 3,3,3-trifluoro-2-[2-(3-trifluoromethyl-phenyl)-morpholin-4-ylmethyl]-propyl ester as a colorless oil. MH+=436.

Workup

  1. customto give a colorless solution
  2. customthe resulting reaction mixture
  3. washwashed with sat. NaHCO3 solution
  4. washby washing with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6a43035d99234a92b612b82f907101c3
Source dataset
uspto-grants-2016_07
Patent number
US09388172B2

Reaction notes

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