Glutaric anhydride → 4-Carboxybutyrylalanyl-alanyl Proline Ethylamide

HRID 1583725Notes

Reaction equation

HRID 1583725 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:9]([NH:11][C:12](=[O:28])[C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18](=[O:27])[C@H:19]([CH3:26])[NH:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23])[CH3:10]>CN(C)C=O>[CH2:9]([NH:11][C:12](=[O:28])[C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18](=[O:27])[C@H:19]([CH3:26])[NH:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH:23][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[CH3:10]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 13750002L-Alanyl-L-alanyl-N-ethyl-L-prolinamide

Product 1

HCID 137499884-Carboxybutyrylalanyl-alanyl Proline Ethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.7 g of glutaric anhydride was added to a solution of 4.0 grams of alanyl-alanyl proline ethylamide in 25 ml of dimethylformamide and the reaction solution heated for 1 hour at 60 degrees C. Then, the solution was evaporated and the resultant non-crystalline evaporation residue dissolved in 30 ml of ethyl acetate. After 48 hours of standing at 3 degrees C., 3.6 g of separated product was filtered off with a melting point of 154 to 156 degrees C. ([α]D20 -137.3 degrees (c 0.3; 50% methyl alcohol).

Workup

  1. customThen, the solution was evaporated
  2. dissolutionthe resultant non-crystalline evaporation residue dissolved in 30 ml of ethyl acetate
  3. filtration, 3.6 g of separated product was filtered off with a melting point of 154 to 156 degrees C

Sources & evidence

ORD record
ord-d4f935365d254c8b96c64699c3a783aa
Source dataset
uspto-grants-1985_11
Patent number
US04554100

Reaction notes

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