Citric Acid → tBoc-Lys(Cbz)-Ala-OH

HRID 1858909Notes

Reaction equation

HRID 1858909 reaction equation
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([O:25]C)=[O:24])[CH3:22])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CO>CO.O>[NH:1]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([OH:25])=[O:24])[CH3:22])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 13967293HCID 13967293, compound

Product 1

HCID 13967298tBoc-Lys(Cbz)-Ala-OHYield 55%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of tBoc-Lys(Cbz)-Ala-OMe (6.4545 g, 13.86 mmol) 16 and LiOH (1.004 g, 41.8 mmol) in methanol/water (80/10 mL) was stirred at room temperature for 4 h. The reaction mixture was neutralized with 0.5 N citric acid and methanol was removed under reduced pressure. The resulting aqueous solution was diluted with water and extracted with dichloromethane and ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered, concentrated and dried under vacuum to obtain 17 as a white solid (3.445 g, 55%). The product was used without further purification.

Workup

  1. customwas removed under reduced pressure
  2. additionThe resulting aqueous solution was diluted with water
  3. extractionextracted with dichloromethane and ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under vacuum

Sources & evidence

ORD record
ord-706b319150be4b0eb5001ed501b996a3
Source dataset
uspto-grants-2000_11
Patent number
US06153596

Reaction notes

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