Hydrochloric Acid → 2-Chloro-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide

HRID 1827534ノート

反応式

HRID 1827534 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:32][CH:31]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C2CCCCO2)=[CH:19][CH:18]=1)(=[O:14])=[O:13].Cl>C(O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:34][CH:35]=1)(=[O:14])=[O:13]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 221373332-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide

生成物 1

HCID 221374712-Chloro-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide収率 84%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of crude 2-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide (0.096 g, 0.15 mmol) in 4 mL ethanol was added 1 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 24 hr. and was diluted with 10 mL saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride (2×10 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/methylene chloride) to afford 0.039 g (84%) of the title compound. MS 555.3 (M+1)+

後処理

  1. washThe aqueous solution was washed with methylene chloride (2×10 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-13516c9c7e8d405a8b392c4e49b239a8
出典データセット
uspto-grants-2006_05
特許番号
US07053212B2

反応ノート

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