Water → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide

HRID 1776555ノート

反応式

HRID 1776555 の反応式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:50])[CH:5]=[C:6]([Cl:49])[C:7]=1[CH2:8][C@@H:9]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)[O:10][C:11](=[O:33])[CH2:12][O:13]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>C(Cl)Cl.Br>[Cl:49][C:6]1[CH:5]=[N+:4]([O-:50])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)[O:10][C:11](=[O:33])[CH2:12][OH:13]

参加物

5

反応物 2

HCID 962WaterHCID 86679511(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(trityloxy)acetoxy)ethyl)pyridine 1-oxide

生成物 1

HCID 86679512(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide収率 76%

試薬・触媒・溶媒 2

HCID 260Hydrogen Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(trityloxy)acetoxy)ethyl)pyridine 1-oxide (4.0 g, 5.55 mmol) in DCM (1 Lt) cooled at 0° C., 160 drops of 48% HBr were added, and the reaction was stirred for 1 hour (temperature below 10° C.). Water was added to the mixture, the organic phase was separated, dried over Na2SO4 and evaporated under vacuum (bath temperature=25° C.). The crude compound was dissolved in DCM, and hexanes was added. The white precipitate thus formed was filtered and washed with plenty of hexanes. After drying, (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide was obtained (2.26 g, 4.73 mmol, 76% yield, MS/ESI+ 478.0 [MH]+) and used in the following step without further purification.

後処理

  1. customthe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum (bath temperature=25° C.)
  4. dissolutionThe crude compound was dissolved in DCM
  5. additionhexanes was added
  6. customThe white precipitate thus formed
  7. filtrationwas filtered
  8. washwashed with plenty of hexanes
  9. customAfter drying

出典と根拠

ORDレコード
ord-491b4fc5663d43ed82d4d519a36de860
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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