Citric Acid → HCID 90060384, compound

HRID 1779247Notes

Reaction equation

HRID 1779247 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](=[O:44])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C@@:22]([OH:27])([CH3:26])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](=[O:44])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C@@:22]([OH:27])([CH3:26])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([OH:16])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 90060337HCID 90060337, compound

Product 1

HCID 90060384HCID 90060384, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

No. 5398770 (20 mg, 0.0326 mmol) was dissolved in methanol (0.4 mL), and an aqueous solution of 1 M sodium hydroxide (65 μL, 0.065 mmol) was added. The mixture was stirred at room temperature for 2 hours. To the resulting white suspension was added an aqueous solution of 0.5 M citric acid, and the mixture was extracted with ethyl acetate. The separated organic layer was washed twice with water, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated. The residue was purified by diol thin layer chromatography (dichloromethane/methanol) to obtain the target compound as clear and colorless solid at a yield of 70%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed twice with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by diol thin layer chromatography (dichloromethane/methanol)
  7. customto obtain the target compound as clear and colorless solid at a yield of 70%

Sources & evidence

ORD record
ord-572e7e990bd94d0b82acc4bb7b1e7cff
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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