Phosphate → (1R)-2-{[2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 916826ノート

反応式

HRID 916826 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:6][CH:5]=1.[NH2:18][CH2:19][C@@H:20]([C:22]1[CH:33]=[CH:32][C:25]2[O:26][C:27]([CH3:31])([CH3:30])[O:28][CH2:29][C:24]=2[CH:23]=1)[OH:21].P([O-])([O-])([O-])=O>CN(C=O)C>[NH3:18].[Si:9]([O:8][C:7]1[CH:16]=[CH:17][C:4]([CH2:3][CH2:2][NH:18][CH2:19][C@@H:20]([C:22]2[CH:33]=[CH:32][C:25]3[O:26][C:27]([CH3:30])([CH3:31])[O:28][CH2:29][C:24]=3[CH:23]=2)[OH:21])=[CH:5][CH:6]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

参加物

6

反応物 3

HCID 1061PhosphateHCID 636962(4-(2-Bromoethyl)phenoxy)(tert-butyl)dimethylsilaneHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

生成物 2

HCID 222AmmoniaHCID 69386381(1R)-2-{[2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol収率 142.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

A solution of [4-(2-bromoethyl)phenoxy](tert-butyl)dimethylsilane (479 mg) in DMF (20 ml) under nitrogen was treated with (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (678 mg) and the mixture was stirred at 20° C. for 9.5 h. Phosphate buffer solution (pH 6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water and dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by SPE (10 g). Elution with DCM then DCM-EtOH-0.880 ammonia solution (300:8:1) then (150:8:1) gave the title compound (991 mg). LCMS RT=3.13 min.

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. customSolvent evaporation in vacuo
  5. customgave a residue which
  6. customwas purified by SPE (10 g)
  7. washElution with DCM

出典と根拠

ORDレコード
ord-f47181a2c3224d86a8f8c2923de2290c
出典データセット
uspto-grants-2007_09
特許番号
US07271197B2

反応ノート

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