Citric Acid → N-tert-Butoxycarbonyl-4-(N-tert-Butoxycarbonyl-2-Aminoethyl)-L-Proline

HRID 2185428Notes

Reaction equation

HRID 2185428 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH:10]([CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][N:8]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[C:25]([O:24][C:22]([N:8]1[CH2:9][CH:10]([CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:7]1[C:6]([OH:29])=[O:5])=[O:23])([CH3:27])([CH3:28])[CH3:26]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 70176170N-tert-Butoxycarbonyl-4-[2-(tert-Butoxycarbonylamino)ethyl]-L-Proline Methyl Ester

Product 1

HCID 21341500N-tert-Butoxycarbonyl-4-(N-tert-Butoxycarbonyl-2-Aminoethyl)-L-ProlineYield 108.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (7 mg) was added to a solution of N-tert-butoxycarbonyl-4-[2-(tert-butoxycarbonylamino)ethyl]-L-proline methyl ester (E, 50 mg) in tetrahydrofuran (0.5 mL)-methanol (0.5 mL)-water (0.5 mL). After stirring 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 (52 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-abe212e33dc840ad8cbe8e2b1e33d5d8
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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