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Pyridine → tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

HRID 2075415
ノート
印刷プレビュー

反応式

HRID 2075415 の反応式
[S:1](Cl)(Cl)=[O:2].[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)[C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][OH:16])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].N1C=CC=CC=1>CC#N.C(Cl)Cl.C1COCC1>[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=1)[C@H:14]1[CH2:15][O:16][S:1](=[O:2])[N:17]1[C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:7])[CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86636682tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

生成物 1

HCID 67089512tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide収率 90%

試薬・触媒・溶媒 3

HCID 6342
Acetonitrile
溶媒
2 回
HCID 6344Dichloromethane溶媒2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of thionyl chloride (0.74 mL, 10.1 mmol) in MeCN (12 mL) and DCM (12 mL) at −78° C. was added a solution of tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (1.82 g, 4.05 mmol) in MeCN (20 mL), DCM (20 mL) and THF (4 mL) dropwise via a dropping funnel. After 10 minutes, pyridine (1.82 mL, 22.3 mmol) was added dropwise at −78° C. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo. The residue was taken up in EtOAc (60 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane) to provide the product as a white solid (1.80 g, 90%).

後処理

  1. customThe solvent was removed in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-cd11a6131eb14f6ca856fa22fb907999
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07919504B2

反応ノート

読み込み中…

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