Imidazole → HCID 89463962、化合物

HRID 2167115ノート

反応式

HRID 2167115 の反応式
[NH2:1][C@@H:2]([CH2:13][OH:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.C1COCC1>[Si:20]([O:14][CH2:13][C@H:2]([NH2:1])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734051(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol

生成物 1

HCID 89463962HCID 89463962、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of D-Tryptophanol (1.024 g) and imidazole (403 mg) in DCM (40 ml) and THF (8 ml) was added a solution of tert-butyldimethylsilyl chloride (0.852 g) in DCM (5 ml) dropwise. The reaction was allowed to warm to room temperature overnight. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution and the reaction mixture was extracted with dichloromethane. The aqueous phase was washed with dichloromethane and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with heptane and increasing amounts of ethyl acetate.

後処理

  1. customThe reaction mixture was quenched with a saturated aqueous NaHCO3 solution
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe aqueous phase was washed with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel eluting with heptane
  9. temperatureincreasing amounts of ethyl acetate

出典と根拠

ORDレコード
ord-0205e8313ceb4279a7609d77853c9558
出典データセット
uspto-grants-2015_06
特許番号
US09044463B2

反応ノート

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