Citric Acid → HCID 68591104, compound

HRID 1429149Notes

Reaction equation

HRID 1429149 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]([O:33][CH3:34])[N:30]=[C:29]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:28]=3)[CH2:12]1)[C:8](=[O:41])[NH:7]2)=[O:5])C.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(Cl)Cl.O>[CH3:34][O:33][C:31]1[N:30]=[C:29]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[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:41])[CH2:23]4)[CH2:12]2)[CH:32]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68589639HCID 68589639, compound

Product 1

HCID 68591104HCID 68591104, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Compound 7d (362 mg, 0.644 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. for 72 h. The reaction mixture was acidified by addition of 5% citric acid whereafter DCM was added. The organic layer was separated, dried (MgSO4), filtered and evaporated which gave the title compound (344 mg, 100%), MS (M+H)+535.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated which

Sources & evidence

ORD record
ord-5e2f74318cf3456792b563324e0042e8
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

Loading…