Diisopropylethylamine → tert-butyl (2R,3R,4S)-5-azido-3-(tert-butyldimethylsilyloxy)-1-hydroxy-4-methylpentan-2-ylcarbamate

HRID 924426ノート

反応式

HRID 924426 の反応式
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[N:18]([CH2:21][C@H:22]([CH3:46])[C@H:23]([C@H:32]1[CH2:36][O:35]C(C)(C)[N:33]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[N+:19]=[N-:20].CCN(C(C)C)C(C)C.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CCO>[N:18]([CH2:21][C@H:22]([CH3:46])[C@@H:23]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[C@H:32]([NH:33][C:39](=[O:40])[O:41][C:42]([CH3:45])([CH3:43])[CH3:44])[CH2:36][OH:35])=[N+:19]=[N-:20]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59226479(R)-tert-butyl 4-((1R,2S)-3-azido-1-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

生成物 1

HCID 86639730tert-butyl (2R,3R,4S)-5-azido-3-(tert-butyldimethylsilyloxy)-1-hydroxy-4-methylpentan-2-ylcarbamate収率 56%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Pyridinium p-toluenesulfonate (1.3 g, 5.2 mmol) was added to a solution of tert-butyl (4R)-4-((1R,2S)-3-azido-1-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.09 g, 2.6 mmol) in EtOH (15 mL). The mixture was heated under reflux for 2 days. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (25 mL), and DIPEA (0.67 mL, 3.8 mmol) was added followed by Boc2O (0.67 g, 3.1 mmol). The mixture was stirred at room temperature for 5 h, and then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-25% EtOAc in hexanes) to provide the sub-title compound (0.56 g, 56%). LCMS calc. for C12H29N4O2Si (M+H-Boc)+: m/z=289.2. found 289.2.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 days
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (25 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluting with 0-25% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9e42a8e061244ab5904c8de96a74b515
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

読み込み中…