Hydrochloric Acid → HCID 15547268, compound

HRID 650659Notes

Reaction equation

HRID 650659 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17]([N:19]([CH2:44][CH3:45])[CH2:20][C:21]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:40]([O:42]C)=[O:41])[CH2:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:30])[CH2:25][C:26](=[O:28])[OH:27])=[O:22])=[O:18])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].Cl>CO.O>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][C:17]([N:19]([CH2:44][CH3:45])[CH2:20][C:21]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:30])[CH2:25][C:26](=[O:27])[OH:28])=[O:22])=[O:18])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131721106HCID 131721106, compound

Product 1

HCID 15547268HCID 15547268, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[N-[N-(4-(N-BOC-piperidin-4-yl)butanoyl)-N-ethylglycyl]aspartyl(b-benzyl ester)]-b-cyclohexylalanine, methyl ester (1.79 g) is dissolved in methanol (40 ml) and 10% palladium/carbon (0.25 g) is added. The mixture is shaken under hydrogen at 50 psi for about 18 hours. The mixture is filtered through a Celite pad and the filtrate evaporated in vacuo to give N-[N-[N-(4-(N-BOC-piperidin-4-yl)butanoyl)-N-ethylglycyl]aspartyl]-b-cyclohexylalanine, methyl ester. The ester is dissolved in methanol (20 ml) and 1N aqueous sodium hydroxide solution (10 ml) is added. The mixture is stirred at room temperature for about 4 hours, diluted with water (25 ml), and acidified to pH 2 with 1N HCl. The mixture is extracted with ethyl acetate (3×100 ml) and the ethyl acetate solution dried over magnesium sulfate, filtered and evaporated in vacuo to give N-[N-[N-(4-(N-BOC-piperidin-4-yl)butanoyl)-N-ethylglycyl]aspartyl]-b-cyclohexylalanine.

Workup

  1. extractionThe mixture is extracted with ethyl acetate (3×100 ml)
  2. dry with materialthe ethyl acetate solution dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1bdba29812db492cb5489ae92c2ac996
Source dataset
uspto-grants-2001_08
Patent number
US06274705B1

Reaction notes

Loading…