HCID 54024474, compound → HCID 53809364, compound

HRID 1249221Notes

Reaction equation

HRID 1249221 reaction equation
C([O:8][C:9](=[O:49])[CH2:10][C@H:11]([NH:29][C:30](=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:12](=[O:28])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[C:37]([NH:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]([NH:29][C@H:11]([C:12](=[O:28])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:10][C:9]([OH:49])=[O:8])=[O:48])(=[O:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 1

HCID 54024474HCID 54024474, compound

Product 1

HCID 53809364HCID 53809364, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Precipitates thus formed were removed by filtration, the filtrate was washed with water, dried over anhydrous magnesium sulfate, concentrated, and subjected to silica gel column chromatography. The product was eluted with ethyl acetate-chloroform (1:9--1:1 by v/v ratio) to provide 600 mg of (S)-3-(6-decanamidohexanamido)-3-tetradecylcarbamoylpropionic acid benzyl ester. 1.00 g of the ester compound obtained was dissolved in a mixture of 30 ml of tetrahydrofuran and 10 ml of methanol and after carrying out catalytic reduction by using 100 mg of 10% Pd-C and removing the catalyst by filtration, the solvent was distilled off to provide 670 mg of (S)-3-(6-decanamidohexanamido)-3-tetradecylcarbamoylpropionic acid.

Workup

  1. customremoving the catalyst
  2. filtrationby filtration
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-745c3e64c375481ea65a73a82f65938f
Source dataset
uspto-grants-1986_12
Patent number
US04629736

Reaction notes

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