Ethyl Acetate → HCID 18652513, compound

HRID 1588242Notes

Reaction equation

HRID 1588242 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][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 80908N-Benzylglycine ethyl esterHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 18652513HCID 18652513, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

CBZ-L-Valine (12.6g, 0.05mol) was dissolved in CH2Cl2 (250mL) and the following reagents were added in equal molar amounts in the stated order; 4-Dimethylaminopyridine (DMAP), ethyl-N-(benzyl)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 IN 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 afforded an oil (17.6 g) which ws used as is for saponification.

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. customIN HCl and separated
  5. extractionThe organic extract
  6. washwas washed with 1N HCl
  7. dry with materialAfter drying over MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-5ffde407bded45429f159996a8f0346d
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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