Ethanol → L-prolyl-L-alanyl-L-proline

HRID 1440056Notes

Reaction equation

HRID 1440056 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-proline

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 crystallizedfrom 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-cb854e1d97f24dcd924680de5b732148
Source dataset
uspto-grants-1996_03
Patent number
US05496927

Reaction notes

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