Ethyl Acetate → [2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester

HRID 2075651Notes

Reaction equation

HRID 2075651 reaction equation
[C:1]([O:5][C:6](=[O:76])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[C:28]([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][O:45]CC2C=CC=CC=2)[CH:27]=[C:26]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][O:68]CC2C=CC=CC=2)[CH:25]=1)([CH3:4])([CH3:3])[CH3:2].[H][H].C(OCC)(=O)C>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:76])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][OH:68])[CH:27]=[C:28]([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:29]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 86607046[2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86607047[2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

In a nitrogen atmosphere, to a suspension of palladium hydroxide (20% by weight; 90 mg) in methanol (2.7 ml), a solution of Compound 48 (500 mg, 0.462 mmol) in methanol (3.6 ml) was added; after the nitrogen atmosphere was replaced with a hydrogen atmosphere, stirring was conducted at room temperature for about 6 hours. After a nitrogen atmosphere was restored, ethyl acetate (about 20 ml) was added, and the mixture was filtered on silica gel and washed with an ethyl acetate solution containing 10% methanol. Concentration under reduced pressure was conducted to yield a crude product of Compound 49.

Workup

  1. filtrationthe mixture was filtered on silica gel
  2. washwashed with an ethyl acetate solution
  3. additioncontaining 10% methanol
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-246d178abd724969ba720fc40df875db
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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