Trifluoroacetic acid → (S)-3,5-dichloro-4-(2-(4-(difluoromethoxy)-3-hydroxyphenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide

HRID 59763ノート

反応式

HRID 59763 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:34])[CH:5]=[C:6]([Cl:33])[C:7]=1[CH2:8][C@@H:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28]CC2CC2)[CH:19]=1)[O:10][C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:12].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:33][C:6]1[CH:5]=[N+:4]([O-:34])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([OH:28])[CH:19]=1)[O:10][C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:12]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 72706559(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide2 回

生成物 1

HCID 86703869(S)-3,5-dichloro-4-(2-(4-(difluoromethoxy)-3-hydroxyphenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide収率 41.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide (180 mg, 0.339 mmol) (Compound 21), prepared as previously described in Example 5, Scheme 5, Table 3, was treated with trifluoroacetic acid (TFA) (4 mL, 51.9 mmol), and the resulting solution was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with CH2Cl2 (40 mL) and washed with water (3×40 mL). The organic layer was died over Na2SO4 and evaporated to dryness. The residue was purified by chromatography on SiO2 (CH2Cl2:AcOEt=3:2) to afford (S)-3,5-dichloro-4-(2-(4-(difluoromethoxy)-3-hydroxyphenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide (83) (67 mg, 0.141 mmol, 41.4% yield, MS/ESI+474.99 [MH]+)

後処理

  1. washwashed with water (3×40 mL)
  2. customevaporated to dryness
  3. customThe residue was purified by chromatography on SiO2 (CH2Cl2:AcOEt=3:2)

出典と根拠

ORDレコード
ord-1456d2fe946c43e7bfd9364c105e5c9c
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

反応ノート

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