2,2-Dimethoxypropane → [1-{5-[1-Benzyloxycarbonylamino-2-(4-tert-butoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(4-tert-butoxy-phenyl)-ethyl]-carbamic Acid Benzyl Ester

HRID 1993124노트

반응식

HRID 1993124 반응식
[CH2:1]([O:8][C:9](=[O:52])[NH:10][CH:11]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:43][CH:42]=1)[CH:12]([OH:39])[CH:13]([OH:38])[CH:14]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:55](OC)([CH3:57])[CH3:56].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH2:1]([O:8][C:9](=[O:52])[NH:10][CH:11]([CH:12]1[CH:13]([CH:14]([NH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[O:38][C:55]([CH3:57])([CH3:56])[O:39]1)[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:43][CH:42]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68612480HCID 68612480, 화합물

생성물 1

HCID 68613247[1-{5-[1-Benzyloxycarbonylamino-2-(4-tert-butoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(4-tert-butoxy-phenyl)-ethyl]-carbamic Acid Benzyl Ester수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Diol 2.5 (5 g, 7 mmol) is dissolved in acetone (120 mL), 2,2-dimethoxypropane (20 mL), and pyridinium p-toluenesulfonate (120 mg, 0.5 mmol). The resulting solution is refluxed for 30 min., and then concentrated under reduced pressure to almost dryness. The resulting mixture is partitioned between methylene chloride and saturated NaHCO3 aqueous solution, dried, concentrated under reduced pressure, and purified by silica gel column chomatography to afford isopropylidene protected diol 2.6 (4.8 g, 92%).

후처리

  1. temperatureThe resulting solution is refluxed for 30 min.
  2. concentrationconcentrated under reduced pressure to almost dryness
  3. customThe resulting mixture is partitioned between methylene chloride and saturated NaHCO3 aqueous solution
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chomatography

출처 및 근거

ORD 기록
ord-a590914b09ba4b8f96f7aeba5b6d5f89
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649015B2

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