Tert-butoxycarbonylalanine → BOC-D-alanine

HRID 2421806Notes

Reaction equation

HRID 2421806 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=[O:5])[CH3:3]>CN(C1C=CN=CC=1)C.ClCCl>[C:7]([NH:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3])([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:8]

Participants

4

Reactant 1

HCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 637606BOC-D-alanineYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.6 g of (R)-fenchol, 0.14 g of DMAP and 1.0 g of BOC-Ala-OH were dissolved in 30 mL of dichloromethane at 0° C. 2.0 g of EDIC were added and the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was extracted with dichloromethane versus water. The organic layer was washed with 1N HCl, NaHCO3 and brine, dried over MgSO4 and concentrated. The crude product was purified using column chromatography, to give 0.3 g of colorless oil (24%).

Workup

  1. addition2.0 g of EDIC were added
  2. extractionThe reaction mixture was extracted with dichloromethane versus water
  3. washThe organic layer was washed with 1N HCl, NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-1661ec7bae414e06ad3d1c7f849c62d9
Source dataset
uspto-grants-2011_06
Patent number
US07959958B2

Reaction notes

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