Citric Acid → HCID 118235798, compound

HRID 627001Notes

Reaction equation

HRID 627001 reaction equation
[F:1][CH:2]([F:45])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:21]1[N:25]2[CH:26]=[C:27]([C:30]3[CH:31]=[N:32][C:33]([N:36]4[CH2:42][CH2:41][C:40](=[O:43])[NH:39][CH2:38][CH2:37]4)=[N:34][CH:35]=3)[CH:28]=[CH:29][C:24]2=[N:23][C:22]=1[CH3:44])[C:11]([O:13]CC1C=CC=CC=1)=[O:12].O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[F:45][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:21]1[N:25]2[CH:26]=[C:27]([C:30]3[CH:31]=[N:32][C:33]([N:36]4[CH2:42][CH2:41][C:40](=[O:43])[NH:39][CH2:38][CH2:37]4)=[N:34][CH:35]=3)[CH:28]=[CH:29][C:24]2=[N:23][C:22]=1[CH3:44])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 118235620HCID 118235620, compound

Product 1

HCID 118235798HCID 118235798, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 311 (0.219 g, 0.358 mmol) in THF (4 mL) was added lithium hydroxide monohydrate (0.03 g, 0.716 mmol) and the mixture was stirred at room temperature for 4 h. The pH of the mixture was adjusted to ˜6 by the dropwise addition of a 10% aqueous solution of citric acid. The material was concentrated in vacuo, and the residue was washed with acetone, to furnish the title compound (0.135 g, 72%). δH (300 MHz, DMSO-d6) 8.57 (m, 3H), 7.66 (m, 1H), 7.51 (m, OH), 7.41 (dd, OH, J 9.3, 1.5 Hz), 7.23 (m, 1H), 7.09 (m, 2H), 6.99 (m, OH), 5.31 (m, OH), 3.95 (d, 4H, J 3.9 Hz), 3.20 (m, 2H), 2.25 (s, 3H). LCMS (pH 10): MH+ 523.2, RT 1.05 minutes.

Workup

  1. concentrationThe material was concentrated in vacuo
  2. washthe residue was washed with acetone

Sources & evidence

ORD record
ord-7deec16a4e58478287a0f8a314fcc456
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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