Sodium hydride → HCID 69200239, compound

HRID 2252256Notes

Reaction equation

HRID 2252256 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[CH2:26][C:25]4[C:20](=[CH:21][C:22]([O:29][CH2:30][CH2:31][N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)=[C:23]([O:27][CH3:28])[CH:24]=4)[C:17]=3[NH:18][N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:40][Si:41]([CH3:48])([CH3:47])[CH2:42][CH2:43][O:44][CH2:45]Cl>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]3[CH2:26][C:25]4[C:20](=[CH:21][C:22]([O:29][CH2:30][CH2:31][N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)=[C:23]([O:27][CH3:28])[CH:24]=4)[C:17]=3[N:18]([CH2:45][O:44][CH2:43][CH2:42][Si:41]([CH3:48])([CH3:47])[CH3:40])[N:19]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 69199291HCID 69199291, compound

Product 1

HCID 69200239HCID 69200239, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of Example 301C (7.71 g, 15.56 mmol) in DMF (200 mL) was added 95% NaH (0.412 g, 16.34 mmol). After 0.5 hour, 2-(trimethylsilyl)ethoxymethyl chloride (2.89 mL, 16.34 mmol) was added dropwise. Then the reaction was run at room temperature for 2 hours. All the DMF was removed. The residue was purified by flash chromatography to give the desired product (5.50 g, 56%). MS (APCI) m/z 626 (M+H)+.

Workup

  1. waitThen the reaction was run at room temperature for 2 hours
  2. customAll the DMF was removed
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d792ce05c20a426c83d07aebccc7b2e2
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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