Citric Acid → HCID 86722307, compound

HRID 874818Notes

Reaction equation

HRID 874818 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10]1[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=1)[O:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:10]1[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=1)[O:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86722308HCID 86722308, compound

Product 1

HCID 86722307HCID 86722307, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 4-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)-2-methoxybenzoate (0.90 g, 1.89 mmol) in a mixture of THF (9 mL) and methanol (9 mL) was added aqueous 2 M sodium hydroxide (9 mL). The reaction mixture was stirred at RT for 18 hours. 10% aqueous citric acid was added to the reaction mixture to pH 3. The mixture was extracted with ethyl acetate (×2). The combined organic phases were washed with brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the title compound (0.82 g, 87%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-0ad8ee32139c4d1daec87b6a2b5e7742
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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