2,6-Dichlorophenol → (R)-tert-butyl 1-(2,6-dichlorophenoxy)propan-2-ylcarbamate

HRID 1053677ノート

反応式

HRID 1053677 の反応式
Br[CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[OH:27]>CC(C)=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[O:27][CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

参加物

5

反応物 3

HCID 68992,6-DichlorophenolHCID 10796Cesium carbonateHCID 57081792(R)-tert-butyl 1-bromopropan-2-ylcarbamate

生成物 1

HCID 86731077(R)-tert-butyl 1-(2,6-dichlorophenoxy)propan-2-ylcarbamate収率 32.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Intermediate 7A (230 mg, 0.970 mmol), cesium carbonate (409 mg, 1.26 mmol) and 2,6-dichlorophenol (157 mg, 0.970 mmol) were heated in acetone (1 mL) under microwave irradiation at 100° C. for 30 min. The solvents were removed and CH2Cl2 was added. The organic phase was washed with H2O, dried over Na2SO4, filtered and concentrated. The colorless oil was purified by flash chromatography (hexanes/EtOAc) to give Intermediate 7B (100 mg, 0.312 mmol, 32.3% yield). LC-MS 219.9 (M-Boc+H), RT=2.23 min (Method B).

後処理

  1. customThe solvents were removed
  2. additionCH2Cl2 was added
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe colorless oil was purified by flash chromatography (hexanes/EtOAc)

出典と根拠

ORDレコード
ord-80ad0e735bf64f84bab9c8383fcac098
出典データセット
uspto-grants-2016_07
特許番号
US09394260B2

反応ノート

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