Z-Val-ONp → Z-Val-Gly-Ala-Pro-OtBu

HRID 971574Notes

Reaction equation

HRID 971574 reaction equation
[CH3:1][CH:2]([C@H:4]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:5]([O:7]C1C=CC([N+]([O-])=O)=CC=1)=O)[CH3:3].[NH2:28][CH2:29][C:30]([NH:32][C@H:33]([C:35]([N:37]1[CH2:48][CH2:47][CH2:46][C@H:38]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:36])[CH3:34])=[O:31]>C(OCC)(=O)C>[NH:17]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[C@H:4]([C:5]([NH:28][CH2:29][C:30]([NH:32][C@H:33]([C:35]([N:37]1[CH2:48][CH2:47][CH2:46][C@H:38]1[C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])=[O:36])[CH3:34])=[O:31])=[O:7])[CH:2]([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 112124Z-Val-ONpHCID 131709997H-Gly-Ala-Pro-OtBu

Product 1

HCID 131709999Z-Val-Gly-Ala-Pro-OtBu

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.73 g of Z-Val-ONP and 2.99 g of H-Gly-Ala-Pro-OtBu in 12 ml of ethyl acetate are stirred for one hour at 0° C. and 20 hours at room temperature. After dilution with ethyl acetate the mixture is washed with 50% saturated potassium carbonate solution and water, dried over sodium sulphate and evaporated at 30° C. in a waterpump vacuum. The oil is crystallised from methanol-water. Melting point 73°-75° C. In a thin layer chromatogram on silica gel Rf = 0.42 in the system toluene-acetone (1:1) and Rf = 0.46 in the system chloroform-methanol (9:1).

Workup

  1. washAfter dilution with ethyl acetate the mixture is washed with 50% saturated potassium carbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated at 30° C. in a waterpump vacuum
  4. customThe oil is crystallised from methanol-water

Sources & evidence

ORD record
ord-f08ca1abe5fd4938940968c748b2e0eb
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

Loading…