L-Alanyl-L-proline → N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline

HRID 2418448Notes

Reaction equation

HRID 2418448 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][CH2:24][C:25](=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:15]1>C(O)C.[Pd]>[CH2:29]([O:28][C:26]([CH:25]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:24][CH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][CH:15]=1)=[O:27])[CH3:30]

Participants

5

Reactant 2

HCID 83525L-Alanyl-L-prolineHCID 127184684-(1H-indol-3-yl)-2-oxo-butyric acid ethyl ester

Product 1

HCID 12718471N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of L-alanyl-L-proline (0.35 g) and ethyl 4-(3-indolyl)-2-oxobutyrate (1.0 g) in 30 ml of ethanol was hydrogenated with 10% Pd on carbon in the presence of 3.2 g of powdered molecular sieves (4A) under 40 lbs of hydrogen pressure. After the reaction was complete the slurry was filtered and the filtrate concentrated to dryness. The residual oil was dissolved in 5 ml of methanol and chromatographed on a Sephadex LH-20 column to yield 0.67 g of crude product as an orange oil. A portion of the crude (0.3 g) was purified by solution in water and extraction with ether. Product was recovered by dilution of the aqueous phase with an equal volume of saturated NaCl solution and extraction with ethyl acetate to yield 80 mg of (N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline as a yellow oil. Mass spectral analysis showed peaks at 559 for the di-silylated product and at 631 for the tri-silylated product.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate concentrated to dryness
  3. dissolutionThe residual oil was dissolved in 5 ml of methanol
  4. customchromatographed on a Sephadex LH-20 column
  5. customto yield 0.67 g of crude product as an orange oil
  6. customA portion of the crude (0.3 g) was purified by solution in water
  7. extractionextraction with ether
  8. customProduct was recovered by dilution of the aqueous phase with an equal volume of saturated NaCl solution and extraction with ethyl acetate

Sources & evidence

ORD record
ord-268b72fb88ff42b9b2f235dcf95a99a4
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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