[2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]acetic acid tert-butyl ester → [2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]acetic acid tert-butyl ester

HRID 2075638Notes

Reaction equation

HRID 2075638 reaction equation
[C:1]([O:5][C:6](=[O:48])[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]=[CH:28][C:27]([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][N:45]=[N+]=[N-])=[CH:26][CH:25]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:48])[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]=[CH:26][C:27]([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][NH2:45])=[CH:28][CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86607044[2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]acetic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67089348[2-(2-{2-[2-(2-{4-[2-(2-{2-[2-(2-Amino-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; 18 mg) in methanol (1 ml), a solution of Compound 27 (190 mg, 0.323 mmol) in methanol (1.5 ml) was added; after the nitrogen atmosphere was replaced with a hydrogen atmosphere, stirring was conducted at room temperature for 1 hour. After a nitrogen atmosphere was restored, insoluble matter was separated by filtration on Celite and washed with methanol. Concentration under reduced pressure was conducted to yield a crude product of Compound 28.

Workup

  1. custominsoluble matter was separated by filtration on Celite
  2. washwashed with methanol
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-54e0ddc5357a4588a8010a2ac3676e87
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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