Ethyl Acetate → HCID 18652517, compound

HRID 1588233Notes

Reaction equation

HRID 1588233 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:30])[CH2:23][NH:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:20].C(OCC)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.Cl>[CH2:19]([O:21][C:22](=[O:30])[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[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:20]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 726987N-Carbobenzoxy-L-valineHCID 13089662HCID 13089662, compound

Product 1

HCID 18652517HCID 18652517, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

CBZ-L-Valine (15.1 g, 0.06 mol) was dissolved in CH2Cl2 (250 mL) and the following reagents were added in equal molar amounts in the stated order; 4-Dimethylaminopyridine (DMAP), ethyl-N-(cyclopentyl)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 diluted with HCl (4:1) 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 an oil (25.1 g) which was purified over silica gel using CH2Cl2 as eluent. The product was collected (6.6 g) as a semisolid. (Rf=0.3, silica gel, CH2Cl2 :CH3OH; 97:3).

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. customseparated
  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-b51ae0e6468c4e578854b842c620f0c1
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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