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

HRID 1669501노트

반응식

HRID 1669501 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-042d250059204e6aa413fac8f7ceb50f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989480B2

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