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

HRID 59763노트

반응식

HRID 59763 반응식
[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]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 72706559(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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]+)

후처리

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

출처 및 근거

ORD 기록
ord-1456d2fe946c43e7bfd9364c105e5c9c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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