Citric Acid → 1-(1,1-Dimethylethyl) (2S,4S)-4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)-1,2-pyrrolidinedicarboxylate

HRID 2185426Notes

Reaction equation

HRID 2185426 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][C@@H:10]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][N:8]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[C:24]([O:23][C:21]([N:8]1[CH2:9][C@H:10]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][C@H:7]1[C:6]([OH:28])=[O:5])=[O:22])([CH3:26])([CH3:27])[CH3:25]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21341550N-tert-Butoxycarbonyl-trans-4-(N-tert-Butoxycarbonylaminomethyl)-L-Proline Methyl Ester

Product 1

HCID 213415491-(1,1-Dimethylethyl) (2S,4S)-4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)-1,2-pyrrolidinedicarboxylateYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (29 mg) was added to a stirred solution of trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-proline methyl ester (C, 204 mg) in tetrahydrofuran (1 mL)-methanol (1 mL)-water (1 mL) at 0° C. The mixture was stirred at room temperature for 4 hr. The reaction mixture was acidified with 10% citric acid and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (167 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-88e3fef7040a4bf29c18a18ce9218751
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…