Citric Acid → 2-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid

HRID 1178001Notes

Reaction equation

HRID 1178001 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:26])[C:6]([NH:9][C:10](=[O:25])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)([CH3:8])[CH3:7].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:6]([CH3:8])([CH3:7])[C:5]([OH:26])=[O:4])=[O:25])=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 578556732-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid methyl ester

Product 1

HCID 578556642-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (38.5 mg, 0.9 mmol) was added to a stirred solution of 2-(4-benzyloxy-benzoylamino)-2-methyl-propionic acid methyl ester (200 mg, 0.6 mmol) in THF:MeOH:H2O (3:1:1, 3.5 mL), and the resulting mixture was stirred at room temperature for 4 hrs. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added, acidified it with aqueous citric acid solution and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 170 mg (90% yield) of 2-(4-benzyloxy-benzoylamino)-2-methyl-propionic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4d29fc592ca44b9a4a7ba6f89b4fc97
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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