Triethylamine → HCID 11965296, compound

HRID 1441534Notes

Reaction equation

HRID 1441534 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17]C(=O)C.[CH3:22]CN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl.CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([O:12][CH3:22])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH2:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 591644842-Acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 11965296HCID 11965296, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (600 mg, 1.97 mmol) and Et3N (412 μL, 3.0 mmol) in DCM (6 mL) was cooled to 0° C. and treated with methanesulfonyl chloride (194 μL, 2.46 mmol) dropwise. The mixture was allowed to warm to r.t. and stirred for 2 h. The mixture was then diluted with DCM, and washed once with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown oil which was taken up in MeOH. This solution was allowed to stand for 60 h at r.t. The mixture was then concentrated in vacuo and the crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 5:1) to give 2-amino-5-(1-methoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (196 mg, 0.71 mmol, 36%) as a white powder, m.p. 112-114° C., ESI-MS: m/z 278 [M+H]+.

Workup

  1. washwashed once with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil which
  6. waitto stand for 60 h at r.t
  7. concentrationThe mixture was then concentrated in vacuo
  8. customthe crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 5:1)

Sources & evidence

ORD record
ord-4dc9555fcfef469692451811b1a8676c
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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