Trifluoroacetic acid → HCID 178504752、化合物

HRID 545987

反応式

HRID 545987 の反応式
C(OC([N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:33])[C@@H:15]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[C:24]([Cl:32])[CH:23]=2)[CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:32][C:24]1[CH:23]=[C:22]([C@@H:15]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[C:14]([NH:13][C:10]2[CH:11]=[CH:12][NH:8][N:9]=2)=[O:33])[CH:27]=[CH:26][C:25]=1[S:28]([CH3:31])(=[O:30])=[O:29]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 671887073-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 178504752HCID 178504752、化合物収率 58.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

3-[2(R)-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazole-1-carboxylic acid tert-butyl ester (1.72 g, 3.47 mmol) was dissolved in methylene chloride (12 mL) and trifluoroacetic acid (4 mL) was added. The solution was stirred at 25° C. for 4 h. The mixture was concentrated in vacuo and the resulting oil was dissolved in ethyl acetate (25 mL), washed with saturated aqueous sodium bicarbonate solution (2×15 mL), saturated aqueous brine solution (2×15 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to produce a yellow oil. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 120 g; 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(1H-pyrazol-3-yl)-propionamide as a white foam (802 mg, 58%) ESI-LRMS m/e calcd for C18H22ClN3O3S [M+] 395.1, found 396.0 [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 1.00-1.19 (m, 2H, CH2), 1.34-1.91 (m, 8H, 4×CH2), 2.08-2.29 (m, 1H, CH), 3.24 (s, 3H, SO2CH3), 3.65 (t, J=7.6 Hz, 1 H, CH), 6.54 (d, 1H, J=1.7, Ar), 7.39 (m, 2H, Ar), 7.54 (d, Jm=1.3 Hz, 1H, Ar), 7.94 (d, Jo=8.2 Hz, 1H, Ar), 9.26 (s, 1H, NH).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe resulting oil was dissolved in ethyl acetate (25 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (2×15 mL), saturated aqueous brine solution (2×15 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto produce a yellow oil
  8. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 120 g; 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c99a3d12a9564f55a9054595d540bed8
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

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