Hydrochloric Acid → HCID 20691748, compound

HRID 1368926Notes

Reaction equation

HRID 1368926 reaction equation
C[O:2][C:3](=[O:47])[C@H:4]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:46])/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[C:34]1[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=1)[NH:5][C:6](=[O:23])/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1.[OH-].[K+].Cl>CO.O1CCCC1>[CH3:22][O:21][C:13]1[CH:12]=[C:11](/[CH:10]=[CH:9]/[CH:8]=[CH:7]/[C:6]([NH:5][C@H:4]([C:3]([OH:47])=[O:2])[CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:46])/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[C:34]2[CH:35]=[C:36]([O:44][CH3:45])[C:37]([O:42][CH3:43])=[C:38]([O:40][CH3:41])[CH:39]=2)=[O:23])[CH:16]=[C:15]([O:17][CH3:18])[C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 20691749HCID 20691749, compound

Product 1

HCID 20691748HCID 20691748, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Added to a solution of 265 mg (0.40 mmol) of Nα,Nε-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-lysine methyl ester synthesized by the process of Example 9 in methanol-tetrahydrofuran (1 ml-1 ml) was 1.0 ml (5.0 mmol) of a 5N aqueous solution of potassium hydroxide, and the mixture was stirred for 3 hours at room temperature. A saturated saline solution (3 ml) and concentrated hydrochloric acid (0.5 ml) were added to the reaction mixture to conduct extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil (234 mg) was purified by column chromatography on silica gel to obtain 203 mg (yield: 80%) of the title compound as a colorless amorphous powder.

Workup

  1. extractionextraction with chloroform
  2. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant crude oil (234 mg) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f9b0e5eb4f8d4652903f0bc739aece59
Source dataset
uspto-grants-2003_06
Patent number
US06576642B2

Reaction notes

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