2,2-Dimethoxypropane → tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1669501ノート

反応式

HRID 1669501 の反応式
[C:1]([NH:8][C@H:9]([CH2:18][OH:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CO[C:22](OC)([CH3:24])[CH3:23]>C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[C:4]([O:3][C:1]([N:8]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:18][O:19][C:22]1([CH3:24])[CH3:23])=[O:2])([CH3:5])([CH3:7])[CH3:6]

参加物

5

反応物 2

HCID 64952,2-DimethoxypropaneHCID 15934817tert-butyl N-((2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)carbamate

生成物 1

HCID 10425336tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate収率 83%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of Boc-L-Tyrosinol (1 g, 3.74 mmol), p-toluenesulfonic acid (0.0356 g, 0.187 mmol), and dichloromethane (DCM) (7.66 mL) was added 2,2 dimethoxypropane (2.3 mL, 18.7 mmol). The resulting mixture was stirred overnight at room temperature under nitrogen. Reaction mixture was washed with sodium bicarbonate (20 mL). Organic layer was separated and washed with sodium bicarbonate (20 mL). The sodium bicarbonate layers were combined and washed with DCM (20 mL). DCM layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to obtain a crude mixture that was purified by silica gel flash chromatography, using EtOAc/hexane (gradient system) to obtain product (0.87 g, 83%): 1H NMR (400 MHz, CDCL3): δ 1.42-1.68 (m, 15H), 2.57-2.63 (m, 1H), 3.00-3.14 (m, 1H), 3.74-3.80 (m, 2H), 3.91-4.05 (m, 1H), 6.77 (t, 2H, J=8.8 Hz), 7.08 (dd, 1H, J=8.0 Hz, J=16 Hz).

後処理

  1. customReaction mixture
  2. washwas washed with sodium bicarbonate (20 mL)
  3. customOrganic layer was separated
  4. washwashed with sodium bicarbonate (20 mL)
  5. washwashed with DCM (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain a crude mixture that
  10. customwas purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-042d250059204e6aa413fac8f7ceb50f
出典データセット
uspto-grants-2011_08
特許番号
US07989480B2

反応ノート

読み込み中…