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Ethyl Acetate → (S)-4-(2-(4-aminobenzylcarbamoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

HRID 1776463
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HRID 1776463 반응식
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:40])[CH:5]=[C:6]([Cl:39])[C:7]=1[CH2:8][C@@H:9]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH:25]=1)[O:10][C:11](=[O:23])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1.CCOC(C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:11]([O:10][C@H:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:32])[F:33])=[C:26]([O:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[CH:25]=2)[CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][N+:4]([O-:40])=[CH:5][C:6]=2[Cl:39])=[O:23])=[CH:19][CH:18]=1
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참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 86679419(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-nitrobenzylcarbamoyloxy)ethyl)pyridine 1-oxide

생성물 1

HCID 86679420(S)-4-(2-(4-aminobenzylcarbamoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide수율 100%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 516892
Sodium Bicarbonate
용매

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온도
60 °C

실험 절차

To a stirred solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-nitrobenzylcarbamoyloxy)ethyl)pyridine 1-oxide (200 mg, 0.334 mmol) in THF (10 ml), SnCl2 dihydrate (603 mg, 2.67 mmol) was added, and the mixture was stirred at 60° C. for 5 hours, then the mixture was diluted with NaHCO3 sat (pH=7) followed by the addition of EtOAc and filtered trough a celite pad. The inorganic phase was extracted with EtOAc. The combined organic layers were rinsed with brine, dried over Na2SO4 and evaporated affording the desired product (190 mg, 0.334 mmol, 100% yield, MS/ESI+ 568.3 [MH]+).

후처리

  1. filtrationfiltered trough a celite pad
  2. extractionThe inorganic phase was extracted with EtOAc
  3. washThe combined organic layers were rinsed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-2e9a96e59e0e48c6a71cebfc6b589085
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09265768B2

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