Sodium hydride → [2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]acetic acid tert-butyl ester

HRID 2075635Notes

Reaction equation

HRID 2075635 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45])=[CH:28][CH:27]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:48]([O:52][C:53](=[O:56])[CH2:54]Br)([CH3:51])([CH3:50])[CH3:49]>C1COCC1.CN(C=O)C.C1COCC1>[C:48]([O:52][C:53](=[O:56])[CH2:54][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:47][CH:46]=1)([CH3:51])([CH3:50])[CH3:49]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 586877442-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)ethanol

Product 1

HCID 67089397[2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]acetic acid tert-butyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To an ice-cooled suspension of sodium hydride (180 mg, 4.5 mmol; 60% in mineral oil) in THF/DMF (5/1 mixed solution 7 ml), a solution of Compound 24 (817 mg, 1.28 mmol) in THF (6 ml) was gradually added; this was followed by stirring for 30 minutes. A solution of bromoacetic acid tert-butyl ester (1.0 g, 5.1 mmol) in THF (7 ml) was added thereto. After the ice bath was removed, stirring was further conducted at room temperature for 2 hours. Water was carefully added to stop the reaction, this was followed by extraction from ethyl acetate, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate solution containing 5% methanol)) to yield Compound 25 (light-yellow oil 655 mg, 68%).

Workup

  1. customAfter the ice bath was removed
  2. stirringstirring
  3. waitwas further conducted at room temperature for 2 hours
  4. additionWater was carefully added
  5. customthe reaction
  6. extractionthis was followed by extraction from ethyl acetate
  7. washthe combined organic phases were washed with saturated brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration and concentration under reduced pressure
  10. customthe residue obtained
  11. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate solution containing 5% methanol))

Sources & evidence

ORD record
ord-00062b2b578d48ce8918f1ca42fdb69e
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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