L-Prolinamide → HCID 12807324, compound

HRID 971562Notes

Reaction equation

HRID 971562 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH2:5])=[O:4].[CH3:9][C@H:10]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:11](OC1C=CC([N+]([O-])=O)=CC=1)=[O:12]>CN(C)C=O>[NH:23]([C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C@H:10]([C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH2:5])=[O:4])=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 111306L-ProlinamideHCID 70218781168-87-2

Product 1

HCID 12807324HCID 12807324, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.28 g of H-Pro-NH2 and 7.57 g of Z-Ala-ONP are dissolved in 20 ml of dimethylformamide and the yellow solution is left standing at room temperature for 18 hours. It is then evaporated to dryness in a high vacuum, the residue is mixed with ether and the resulting powder is thoroughly triturated. After filtering off and drying, 5.5 g of Z-Ala-Pro-NH2 of melting point 167.5°-168.5° C. are obtained. [α]D20 = -74° (c = 1 in methanol).

Workup

  1. waitthe yellow solution is left
  2. customIt is then evaporated to dryness in a high vacuum
  3. additionthe residue is mixed with ether
  4. customthe resulting powder is thoroughly triturated
  5. filtrationAfter filtering off
  6. customdrying

Sources & evidence

ORD record
ord-84739d0d18d74249b810c59f940b3d16
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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