Ethyl alpha-oxobenzenebutanoate → HCID 22827210, compound

HRID 1463027Notes

Reaction equation

HRID 1463027 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].C1([C@@H]2CN[C@H](C(O)=O)C2)C=CC=CC=1.N[C@H](C(N1C[C@@H](CC2C=CC=CC=2)C[C@H]1C(O)=O)=O)C.O=[C:55]([CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:56]([O:58][CH2:59][CH3:60])=[O:57]>[Pd].C(O)C>[CH2:59]([O:58][C:56]([C@@H:55]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:57])[CH3:60]

Participants

7

Reactant 4

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 11160513HCID 11160513, compoundHCID 22827195HCID 22827195, compoundHCID 70443362HCID 70443362, compound

Product 1

HCID 22827210HCID 22827210, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.85 grams of 1-(L-alanyl)-4-(R)-phenyl-L-proline [prepared by employing cis-4-phenyl-L-proline in the procedure of Example 2(a) to (d)], 0.2 grams of ethyl 2-oxo-4-phenylbutyrate and 1.5 grams of molecular sieves in 10 ml. of ethanol is hydrogenated under 40 psi with 1 gram of 10% palladium on carbon as the catalyst. The mixture is filtered when the uptake of hydrogen has ceased, and the filtrate is concentrated. The crude product is absorbed on an ion exchange resin (Dowex 50, H+) and eluted with 2% pyridine in water to yield the desired 1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(R)-phenyl-L-proline.

Workup

  1. customprepared
  2. filtrationThe mixture is filtered when the uptake of hydrogen
  3. concentrationthe filtrate is concentrated
  4. customThe crude product is absorbed on an ion exchange resin (Dowex 50, H+)
  5. washeluted with 2% pyridine in water

Sources & evidence

ORD record
ord-aba17faca12a40819652f298f2655515
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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