Citric Acid → HCID 69799959, compound

HRID 1823201Notes

Reaction equation

HRID 1823201 reaction equation
C([O:3][C:4]([C@H:6]1[N:10]2[C:11](=[O:21])[C:12]([NH:16][CH:17]3[CH2:20][CH2:19][CH2:18]3)=[N:13][C:14]([Cl:15])=[C:9]2[C@H:8]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:7]1)=[O:5])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Cl:15][C:14]1[N:13]=[C:12]([NH:16][CH:17]2[CH2:18][CH2:19][CH2:20]2)[C:11](=[O:21])[N:10]2[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][C@@H:8]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:9]=12

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 69798391HCID 69798391, compound

Product 1

HCID 69799959HCID 69799959, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the ester from Step E (78 mg, 0.18 mmol) dissolved in methanol (1.0 mL) was added LiOH (1.0 M, 0.36 mL). The mixture was stirred at rt for 1.5 h. It was acidified with 5% citric acid, and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. Evaporation of solvent and lyopholization gave 70 mg white solid used directly in the next Step.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvent and lyopholization

Sources & evidence

ORD record
ord-1b2629a86e3342ee81f2494fac12ee2e
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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