Citric Acid → HCID 68591013, compound

HRID 1429163Notes

Reaction equation

HRID 1429163 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]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[C:29]([O:39][CH3:40])[N:28]=3)[CH2:12]1)[C:8](=[O:41])[NH:7]2)=[O:5])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH3:40][O:39][C:29]1[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]=[C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:30]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 68590866HCID 68590866, compound

Product 1

HCID 68591013HCID 68591013, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 13d (470 mg, 0.83 mmol) in a mixture of THF methanol 1:1 (30 ml) was added 1 M LiOH solution (10 ml) and the mixture was stirred for four days at room temperature. A 5% solution of citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was dried with sodium sulphate and evaporated on silica gel. The product was isolated by silica gel chromatography eluted with DCM methanol, (400 mg, 88%), (M+H)+535.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. customevaporated on silica gel
  4. customThe product was isolated by silica gel chromatography
  5. washeluted with DCM methanol, (400 mg, 88%)

Sources & evidence

ORD record
ord-ad7b21d674ef483583b1fba2e2235a6d
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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