Triethylamine → HCID 58288540, compound

HRID 1969047Notes

Reaction equation

HRID 1969047 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][OH:24])[CH:7]=1)[CH3:2].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:14]=2[CH2:23][O:24][S:34]([CH3:33])(=[O:36])=[O:35])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 58288493HCID 58288493, compound

Product 1

HCID 58288540HCID 58288540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[3-(2-Hydroxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.355 g, 1.0 mmol) and triethylamine (0.21 mL, 1.5 mmol) were combined in CH2Cl2 (7.2 mL) and cooled to 0° C. Methanesulfonyl chloride (0.09 mL, 1.1 mmol) was added, and the reaction was stirred for 3 hours. Some starting material was still seen by analytical LCMS, so additional methanesulfonyl chloride (0.04 mL) and triethylamine (0.07 mL) was added at 0° C., and the reaction was stirred for another 2 hours. The mixture was partitioned between CH2Cl2 and H2O, and the aqueous layer was separated and extracted twice with CH2Cl2. The combined organic layers were dried and concentrated to give the title compound.

Workup

  1. additionwas added at 0° C.
  2. stirringthe reaction was stirred for another 2 hours
  3. customThe mixture was partitioned between CH2Cl2 and H2O
  4. customthe aqueous layer was separated
  5. extractionextracted twice with CH2Cl2
  6. customThe combined organic layers were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eeae4924519f4525b69d9f416768d373
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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