Citric Acid → HCID 68591016, compound

HRID 1429127Notes

Reaction equation

HRID 1429127 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]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[N:39]=[C:38]([O:48][CH3:49])[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:30]=[CH:31][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]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[N:39]=[C:38]([O:48][CH3:49])[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:27][CH:28]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68592480HCID 68592480, compound

Product 1

HCID 68591016HCID 68591016, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 2c (0.680 mg, 0.996 mmol) was dissolved in a 2:1:1 mixture of THF:MeOH:H2O (144 ml). LiOH (1 M, 10 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 separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography, DCM: MeOH 9:1 which the title compound (380 mg, 58%), MS (M+H)+656.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography, DCM: MeOH 9:1 which the title compound (380 mg, 58%), MS (M+H)+656

Sources & evidence

ORD record
ord-658f0b53cede4198a3483d0d7197c120
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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