Triacetoxyperiodinane → tert-butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-oxobutanoate

HRID 1427288ノート

反応式

HRID 1427288 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([CH2:27][OH:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([CH:27]=[O:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 86705056tert-Butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-hydroxybutanoate

生成物 1

HCID 86705057tert-butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-oxobutanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the product of Step C (1.2 g, 2.4 mmol) in DCM (10 mL) was added Dess-Martin periodinane (2.03 g, 4.8 mmol) in portion at room temperature. After stirring for 0.5 h, the mixture was diluted with water (15 mL), extracted with ethyl acetate. The organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/PE=1:8) to afford the title compound. LC/MS m/z=499.2[M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layers were washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography (EA/PE=1:8)

出典と根拠

ORDレコード
ord-88b9efd883d54e3abb9e1f19b056d18d
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

読み込み中…