4-Methylmorpholine → tert-Butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-hydroxybutanoate

HRID 1477911ノート

反応式

HRID 1477911 の反応式
[C:1]([O:5][C:6](=[O:36])[CH2:7][C:8]([N:19]1[C:27]2[C:22](=[C:23]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1)([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.[BH4-].[Na+]>COCCOC>[C:32]([O:31][C:29]([NH:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:22]=1[CH:21]=[CH:20][N:19]2[C:8]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)([CH2:9][OH:10])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:36])=[O:30])([CH3:33])([CH3:34])[CH3:35]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 705646004-tert-butoxy-2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)-4-oxobutanoic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of the product of step B (1.5 g, 2.9 mmol) and NMM (590 mg, 5.83 mmol) in DME (15 mL) was added isobutyl carbonochloridate (793 mg, 5.83 mmol) dropwise at 0° C. After stirring for 30 min. NaBH4 was added to the mixture at 0° C. The resulting mixture was stirred at room temperature for another 1 h, and then quenched with saturated ammonium chloride solution (10 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 (PE:EA=3:1) to afford the title compound as colorless oil. LC/MS m/z=501.2[M+H]+.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for another 1 h
  2. customquenched with saturated ammonium chloride solution (10 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (PE:EA=3:1)

出典と根拠

ORDレコード
ord-aa8846367a6a4d3bbd7fbe84296c21f0
出典データセット
uspto-grants-2016_08
特許番号
US09403807B2

反応ノート

読み込み中…