Ethanol → L-prolyl-L-alanyl-L-proline

HRID 1458180Notes

Reaction equation

HRID 1458180 reaction equation
C([O:8][C:9](=[O:27])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:26])[C@H:16]([CH3:25])[NH:17][C:18](=[O:24])[C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1)C1C=CC=CC=1.C(O)C.[H][H]>>[NH:20]1[CH2:21][CH2:22][CH2:23][C@H:19]1[C:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:27])=[O:8])=[O:26])[CH3:25])=[O:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 86749330L-prolyl-L-alanyl-L-proline benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 9817252L-prolyl-L-alanyl-L-prolineYield 73%

Procedure

Into a Parr flask flushed with argon containing 450 mg of 10% palladium on charcoal catalyst was added a solution of Ac-L-prolyl-L-alanyl-L-proline benzyl ester in (1.0 g, 2.41 mmol) absolute ethanol (100 ml). The contents were shaken under 40 psi of hydrogen overnight at room temperature. The mixture was filtered through celite and the filtrate concentrated on a rotary evaporator to give crude Ac-L-prolyl-L-alanyl-L-proline which was crystallized from tetrahydrofuran-methanol-ether to give the desired product (0.57 g) in 73% yield.

Workup

  1. customInto a Parr flask flushed with argon containing 450 mg of 10% palladium on charcoal catalyst
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-89fbcf6e60ca4bcc930e27c21067ee5d
Source dataset
uspto-grants-1998_12
Patent number
US05849866

Reaction notes

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