Ethyl Acetate → HCID 18652512, compound

HRID 1588244Notes

Reaction equation

HRID 1588244 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][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][N: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])[C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 726987N-Carbobenzoxy-L-valineHCID 54510475HCID 54510475, compound

Product 1

HCID 18652512HCID 18652512, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

CBZ-L-Valine (15.4 g, 0.0612 mol) was dissolved in CH2Cl2 (300 mL) and the following reagents were added in equal molar amounts in the stated order; 4-dimethylaminopyridine (DMAP), ethyl-N-(3-methylpyridinyl)glycinate and WSCDI. 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 with water and separated. The organic extract was washed with water followed by 5% aqueous Na2CO3 and saturated aqueous NaCl-solution. After drying over MgSO4, filtration and evaporation under reduced pressure yielded an oil (11.1 g) which was purified over silica gel using CH2Cl2 : CH3OH 97.3 as eluent. Isolated 9.2 g of an amber oil.

Workup

  1. additionthe following reagents were added in equal molar amounts in the stated order
  2. customEvaporation of the solvent
  3. customyielded a viscous semisolid which
  4. customwith water and separated
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialAfter drying over MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-643456aecdcd4e7ab5ed71bc7257bb64
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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