Citric Acid → HCID 68590619, compound

HRID 1429144Notes

Reaction equation

HRID 1429144 reaction equation
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35][C:36]3[CH:41]=[C:40]([O:42][CH3:43])[N:39]=[C:38]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:37]=3)[CH2:12]1)[C:8](=[O:50])[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>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:15]2[C:14](=[O:34])[N:13]3[CH:9]([CH2:10][CH:11]([O:35][C:36]4[CH:41]=[C:40]([O:42][CH3:43])[N:39]=[C:38]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[N:37]=4)[CH2:12]3)[C:8](=[O:50])[NH:7][C:6]3([C:4]([OH:5])=[O:3])[CH:23]([CH2:24]3)[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68590606HCID 68590606, compound

Product 1

HCID 68590619HCID 68590619, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 6e (410 mg, 0.60 mmol) was dissolved in a 2:1:1 mixture of THF:MeOH:H2O (144 ml). LiOH (1 M, 6 ml) was added and the reaction mixture was stirred at RT over night. 5% Citric acid was added followed by DCM. The organic layer was dried (MgSO4), filtered and evaporated which gave the title compound (305 mg, 78%), MS (M+H)+656.

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. customevaporated which

Sources & evidence

ORD record
ord-4fce611200514de9bb12df4719815ef1
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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