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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
ノート
印刷プレビュー

反応式

HRID 1776463 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 516892
Sodium Bicarbonate
溶媒

反応条件

温度
60 °C

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-2e9a96e59e0e48c6a71cebfc6b589085
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09265768B2

反応ノート

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