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 1993124ノート

反応式

HRID 1993124 の反応式
[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

参加物

5

反応物 3

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

生成物 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 Ester収率 92%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a590914b09ba4b8f96f7aeba5b6d5f89
出典データセット
uspto-grants-2010_01
特許番号
US07649015B2

反応ノート

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