Dimethylformamide → HCID 13749972, compound

HRID 1583723Notes

Reaction equation

HRID 1583723 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH2:8]([NH:10][C:11](=[O:22])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:21])[C@H:18]([CH3:20])[NH2:19])[CH3:9].O1CCOCC1.CN(C)C=O>CO>[CH2:8]([NH:10][C:11](=[O:22])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:21])[C@H:18]([CH3:20])[NH:19][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 312751,4-DioxaneHCID 13945020HCID 13945020, compound

Product 1

HCID 13749972HCID 13749972, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg of succinic anhydride was added to a solution of 500 mg of alanyl proline ethylamide in form of dioxane (10 ml) and 0.25 ml of dimethylformamide and the reaction solution heated under reflux for 30 minutes. Then the solution was evaporated and the residue crystallized from 10 ml of acetone and 30 ml of ether. 510 mg of a product having a melting point of 139 to 141 degrees C. was obtained. [α[D20 -129.2 degrees (c 0.3; 50% methyl alcohol).

Workup

  1. temperaturethe reaction solution heated
  2. temperatureunder reflux for 30 minutes
  3. customThen the solution was evaporated
  4. customthe residue crystallized from 10 ml of acetone and 30 ml of ether
  5. customwas obtained

Sources & evidence

ORD record
ord-e5bbadd394b94339a6d7c100535b9f19
Source dataset
uspto-grants-1985_11
Patent number
US04554100

Reaction notes

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