Sodium hydride → HCID 57936539, compound

HRID 1434858Notes

Reaction equation

HRID 1434858 reaction equation
[CH:1]([Si:4]([O:11][CH2:12][C@@H:13]([OH:23])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[H-].[Na+].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:31]Br>C1COCC1>[CH:8]([Si:4]([O:11][CH2:12][C@@H:13]([O:23][CH2:31][C:30]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:28]([O:27][CH3:26])[CH:29]=1)[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109004583,4-Dimethoxybenzyl bromideHCID 57936617HCID 57936617, compound

Product 1

HCID 57936539HCID 57936539, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. mixture of (2S)-3-(t-butoxycarbonylamino)-2-hydroxypropyl triisopropylsilyl ether (6 g, 17.2 mmol) and THF (35 mL) was added NaH (60% dispersion in oil, hexane washed). The reaction was stirred for 1 h, 3,4-dimethoxy-benzyl bromide (4.3 g, 18.9 mmol) in THF (20 mL) was added, and then stirred at ambient temperature for 18 h. The mixture was concentrated and chromatographed on SiO2 (gradient CH2Cl2 to EtOAc) to give the title compound (1.1 g, 12.8%).

Workup

  1. stirringstirred at ambient temperature for 18 h
  2. concentrationThe mixture was concentrated
  3. customchromatographed on SiO2 (gradient CH2Cl2 to EtOAc)

Sources & evidence

ORD record
ord-ca004f62aef148e0b6e8b74da6ec8645
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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