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2-Azido-2-methylpropanoic acid → 2-(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoic acid

HRID 877357
ノート
印刷プレビュー

反応式

HRID 877357 の反応式
[CH3:1][C:2]([S:5]([NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:13][N:12]=1)[C:9]#[CH:10])=[O:6])([CH3:4])[CH3:3].[N:23]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28])=[N+:24]=[N-:25].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.C(O)(C)(C)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:2]([S:5]([NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])=[CH:13][N:12]=1)[C:9]1[N:25]=[N:24][N:23]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28])[CH:10]=1)=[O:6])([CH3:1])([CH3:3])[CH3:4]
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 128639852-Azido-2-methylpropanoic acidHCID 23667548Sodium AscorbateHCID 866689592-methyl-N-{(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]prop-2-ynyl}propane-2-sulfinamide

生成物 1

HCID 681578412-(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoic acid収率 44%

試薬・触媒・溶媒 3

HCID 24462
Copper Sulfate
触媒
HCID 962Water溶媒
HCID 6386tert-Butanol溶媒

実験手順

To a solution of 0.50 g (1.5 mmol) 2-methyl-N-{(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]prop-2-ynyl}propane-2-sulfinamide in 3.0 mL water and 3.0 mL t-butanol was added 1.8 mL (1.5 mmol) 2-azido-2-methylpropanoic acid, 0.15 mL (0.15 mmol) 1.0M aqueous sodium ascorbate solution, and 15 μL (0.02 mmol) 1.0M solution of aqueous copper (II) sulfate. After 24 h at room temperature, the reaction mixture was quenched with water, acidified with 1N HCl, extracted three times with ethyl acetate, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-20% MeOH:CH2Cl2) afforded 0.30 g (44%) 2-(4-{(S)-[(tert-butylsulfinyl)amino][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoic acid. ES-MS [M+1]+=464.2.

後処理

  1. customthe reaction mixture was quenched with water
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica gel, linear gradient 0-20% MeOH:CH2Cl2)

出典と根拠

ORDレコード
ord-a01cda74f5494766a53ecf3f65f35f0a
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987310B2

反応ノート

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