Ethyl Acetate → HCID 18652515, compound

HRID 1588245Notes

Reaction equation

HRID 1588245 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:19]([O:21][C:22](=[O:32])[CH2:23][NH:24][CH:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:20].C(OCC)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:19]([O:21][C:22](=[O:32])[CH2:23][N:24]([C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 726987N-Carbobenzoxy-L-valineHCID 13145542HCID 13145542, compound

Product 1

HCID 18652515HCID 18652515, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

CBZ-L-Valine (10.05 g, 0.04 mol) was dissolved in CH2Cl2 (300 mL) and the following reagents were added in equal molar amounts in the stated order: 4-Dimethylaminopyridine, ethyl-N-(cycloheptyl)glycinate and WSCDI. Used additional 100 mL CH2Cl2 to wash down the reagents. The reaction mixture was allowed to stir at room temperature over night. Evaporation of the solvent yielded a viscous semisolid which was treated with ethyl acetate and then 1N HCl and separated. The organic extract was washed with 1N HCl followed by 5% aqueous Na2CO3 and saturated aqueous NaCl-solution. After drying over MgSO4, filtration and evaporation under reduced pressure yielded the titled compound as an oil (11.2 g) which was used as is for saponification.

Workup

  1. additionthe following reagents were added in equal molar amounts in the stated order
  2. washUsed additional 100 mL CH2Cl2 to wash down the reagents
  3. customEvaporation of the solvent
  4. customyielded a viscous semisolid which
  5. custom1N HCl and separated
  6. extractionThe organic extract
  7. washwas washed with 1N HCl
  8. dry with materialAfter drying over MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-98be5e3f846343658379d4c2f10cf23b
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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