Citric Acid → 3-{[(Tert-butoxy)carbonyl]amino}-2-({[(tert-butoxy)carbonyl]amino}methyl)propanoic acid

HRID 2357196Notes

Reaction equation

HRID 2357196 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:25])[CH:6]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:21]([O:20][C:18]([NH:17][CH2:16][CH:6]([CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:25])=[O:4])=[O:19])([CH3:23])([CH3:24])[CH3:22]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22251381Methyl 3-((tert-butoxycarbonyl)amino)-2-(((tert-butoxycarbonyl)amino)methyl)propanoate

Product 1

HCID 222513823-{[(Tert-butoxy)carbonyl]amino}-2-({[(tert-butoxy)carbonyl]amino}methyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 2N sodium hydroxide (2.48 mL, 4.96 mmol) was added to a stirring solution of the methyl ester 13 (0.41 g, 1.24 mmol) in THF (7.5 mL) and the mixture was stirred at rt. for 24 h. Water (15 mL) was added and the solution was acidified with 5% aqueous citric acid. The mixture was extracted with CHCl3 (3×25 mL) and the combined organic extracts were washed with brine (30 mL), dried (Na2SO4), and evaporated in vacuo to leave the acid 14 as a viscous, colourless oil (280 mg).

Workup

  1. extractionThe mixture was extracted with CHCl3 (3×25 mL)
  2. washthe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b7025a4755bb4b0688dc4d35c5b5e2e2
Source dataset
uspto-grants-2010_07
Patent number
US07759519B2

Reaction notes

Loading…