Citric Acid → HCID 68591633, compound

HRID 1429136Notes

Reaction equation

HRID 1429136 reaction equation
C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[CH:13]1[CH:9]([CH2:10][CH:11]([O:26][C:27]3[CH:32]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:30]=[C:29]([O:37][CH3:38])[N:28]=3)[CH2:12]1)[C:8](=[O:39])[NH:7]2)=[O:5])C.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[C:33]([C:31]1[N:30]=[C:29]([O:37][CH3:38])[N:28]=[C:27]([O:26][CH:11]2[CH2:10][CH:9]3[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]4[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]3=[O:39])[CH2:23]4)[CH2:12]2)[CH:32]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68589805HCID 68589805, compound

Product 1

HCID 68591633HCID 68591633, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Compound 3i (350 mg, 0.645 mmol) was dissolved in a 2:1:1 mixture of THF:MeOH:H2O (100 ml). LiOH (1 M, 6.5 ml) was added and the reaction mixture was stirred at 60° C. over night. The mixture was acidified by adding citric acid and then extracted three times with EtOAc. The combined organic layers were dried (MgSO4), filtered and evaporated. The afforded residue was purified by column chromatography (DCM/MeOH 98/2→94/6) which gave the title compound (320 mg, 97%), MS (M+H)+515.

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe afforded residue was purified by column chromatography (DCM/MeOH 98/2→94/6) which

Sources & evidence

ORD record
ord-28bead235f5a4ca4b17a193b80052071
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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