Hydrochloric Acid → HCID 68815846、化合物

HRID 732361ノート

反応式

HRID 732361 の反応式
N1C(C)=CC=CC=1C.[Si:9]([O:16]S(C(F)(F)F)(=O)=O)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([F:36])[CH2:33][C@@H:32]1[C@@H:37](O)[C@H:38]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:39]([N:41]1[C@@H:45]([CH:46]([CH3:48])[CH3:47])[CH2:44][O:43][C:42]1=[O:49])=[O:40])=[O:30])([CH3:27])([CH3:26])[CH3:25].Cl>ClCCl>[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([F:36])[CH2:33][C@@H:32]1[C@@H:37]([O:16][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[C@H:38]([CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:39]([N:41]1[C@@H:45]([CH:46]([CH3:47])[CH3:48])[CH2:44][O:43][C:42]1=[O:49])=[O:40])=[O:30])([CH3:26])([CH3:27])[CH3:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 688147272-(R)-[2-(S)-Benzyl-1-(S)-hydroxy-3-(4-(S)-isopropyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl]-4-(R)-fluoropyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 68815846HCID 68815846、化合物収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add 2,6-lutidine (5.3 mL, 54 mmol) and tert-butyl-dimethylsilyl-trifluoromethylsulfonate (1.62 mL, 7.08 mL) to a solution of 2-(R)-[2-(S)-benzyl-1-(S)-hydroxy-3-(4-(S)-isopropyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl]-4-(R)-fluoropyrrolidine-1-carboxylic acid tert-butyl ester (2.585 g, 5.4 mmol) in dichloromethane (40 mL) at −78° C. Stir 3 h, warm to room temperature, stir 5 min and cool in an ice bath. Add 1 N HCl (100 mL), wash with 1 N HCl (2×100 mL), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a white foam (2.779 g, 87%).

後処理

  1. stirringstir 5 min
  2. temperaturecool in an ice bath
  3. washwash with 1 N HCl (2×100 mL), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

出典と根拠

ORDレコード
ord-d92da758cb8c4458917dacd9d90e43b4
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

読み込み中…