2,2-Dimethoxypropane → tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate

HRID 1254362ノート

反応式

HRID 1254362 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][OH:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.B(F)(F)F.CCOCC>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C@H:9]1[CH2:15][O:16][C:19]([CH3:21])([CH3:20])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

参加物

5

反応物 2

HCID 64952,2-DimethoxypropaneHCID 54573797Methyl (S)-3-(Boc-amino)-4-hydroxybutanoate

生成物 1

HCID 10923729tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate収率 92%

試薬・触媒・溶媒 2

HCID 8000Boron trifluoride etherate触媒HCID 180Acetone溶媒

実験手順

To a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxybutanoate (7.0 g, 30.0 mmol) in acetone (90 mL), there was added 2,2-dimethoxypropane (37 mL, 300 mmol) followed by BF3.Et2O (0.11 mL, 0.9 mmol). The resulting solution was stirred at rt overnight. Solvents were removed under vacuum, and the residue was redissolved in ether (100 mL), washed with sat'd NaHCO3 (20 mL). Upon concentrating under vacuum, the residue was purified by flash column chromatography to give (S)-tert-butyl 4-(2-methoxy-2-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylate (7.51 g, 92%). MS m/z 296 (M+Na+).

後処理

  1. customSolvents were removed under vacuum
  2. dissolutionthe residue was redissolved in ether (100 mL)
  3. washwashed with sat'd NaHCO3 (20 mL)
  4. concentrationUpon concentrating under vacuum
  5. customthe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-6316ef4bf1f34b8c8565447ccd5f4e21
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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