HCID 68921116, compound → HCID 58860008, compound

HRID 1785921Notes

Reaction equation

HRID 1785921 reaction equation
[C:1]([N:4]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:28])[CH2:6]1)(=[O:3])[CH3:2]>CCO.C(Cl)Cl.[Pd]>[C:1]([N:4]([C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:28])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 68921116HCID 68921116, compound2×

Product 1

HCID 58860008HCID 58860008, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-propionic acid was prepared from (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid. A solution of (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid (50 mg, 0.102 mmol) in EtOH (2 ml) and CH2Cl2 (10 drops for solubility) was subjected to Pd-C (10%, ca. 50 mg) and 1 atm H2 gas. After 1 hour, the mixture was filtered, concentrated and subjected to silica gel chromatography (2% MeOH in EtOAc to 10% MeOH in EtOAc), to afford the title compound (50 mg, 99%).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4f0a98b5259a41a8ba3de6adcfa42b29
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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