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Citric Acid → 4-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid

HRID 602132
Notes
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Reaction equation

HRID 602132 reaction equation
[OH-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([C:16]([O:18]C)=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 588174744-tert-Butyl 2-methyl morpholine-2,4-dicarboxylate

Product 1

HCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A 1 mol/L aqueous potassium hydroxide solution (3 mL) was added to methyl 4-(tert-butoxycarbonyl)morpholine-2-carboxylate (251 mg, 1.02 mmol) in methanol (15 mL). The mixture was stirred at room temperature for 8 hours. Subsequently, water was added to the mixture, followed by addition of a 5% aqueous citric acid solution to make the mixture acidic. The mixture was then extracted with ethyl acetate. The extract was washed with brine and was dried over magnesium sulfate. Evaporation of the solvent gave 219 mg (93%) of the desired compound as a colorless powder.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialwas dried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-52c0185b802d4cea9b27386c3abe2c19
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902367B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes