Triphenylphosphine → HCID 57595493, compound

HRID 1786030Notes

Reaction equation

HRID 1786030 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]([C@H:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:46]([C:53](=[O:61])[C:54]3[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=3)[C@@H:45]([CH3:62])[CH2:44]2)[C:40](=[O:42])[CH3:41])=[CH:35][CH:34]=1.[CH2:63]([O:65][C:66]([CH:68]1[CH2:73][CH2:72][CH:71](O)[CH2:70][CH2:69]1)=[O:67])[CH3:64]>C1COCC1>[CH2:63]([O:65][C:66]([CH:68]1[CH2:73][CH2:72][CH:71]([O:60][C:57]2[CH:56]=[CH:55][C:54]([C:53]([N:46]3[C:47]4[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@H:43]([N:39]([C:40](=[O:42])[CH3:41])[C:36]4[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][CH:37]=4)[CH2:44][C@@H:45]3[CH3:62])=[O:61])=[CH:59][CH:58]=2)[CH2:70][CH2:69]1)=[O:67])[CH3:64]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 57595493HCID 57595493, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl azodicarboxylate (120 mg) in 5 ml THF at 0° C., was added PPh3 (181 mg). The mixture was stirred for 10 min at 0° C. Then (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (200 mg) was added. The mixture was stirred for 20 min at 0° C. 4-Hydroxy-cyclohexanecarboxylic acid ethyl ester (80 mg) was added. The final reaction mixture was stirred for overnight at RT. The mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with sat. aqueous sodium bicarbonate, brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30/70 hexanes/ethyl acetate gradient) to afford pure (2S,4R)-4-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-cyclohexanecarboxylic acid ethyl ester (100 mg, 37%).

Workup

  1. stirringThe mixture was stirred for 20 min at 0° C
  2. customThe final reaction mixture
  3. stirringwas stirred for overnight at RT
  4. concentrationThe mixture was concentrated under reduced pressure
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with sat. aqueous sodium bicarbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (30/70 hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-706040e5038f4dac820eb79bab8c39b3
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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