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 1993124Notes

Reaction equation

HRID 1993124 reaction equation
[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

Participants

5

Reactant 3

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

Product 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 EsterYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a590914b09ba4b8f96f7aeba5b6d5f89
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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