Triphenylphosphine → (1R,2R,4R)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarboxylic acid methyl ester

HRID 2242429Notes

Reaction equation

HRID 2242429 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][C@H:6]1[C:11](=[O:24])[NH:12][C@H:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][CH3:16])=[O:4].[C:25]1([C:31]2[CH:40]=[C:39](O)[C:38]3[C:33](=[CH:34][C:35]([O:42][CH3:43])=[CH:36][CH:37]=3)[N:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][C:39]2[C:38]3[C:33](=[CH:34][C:35]([O:42][CH3:43])=[CH:36][CH:37]=3)[N:32]=[C:31]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:40]=2)[CH2:7][C@H:6]1[C:11](=[O:24])[NH:12][C@H:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][CH3:16])=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59204201(1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl esterHCID 178487676HCID 178487676, compound

Product 1

HCID 59204183(1R,2R,4R)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarboxylic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 42 (249 mg, 0.725 mmol), 2-phenyl-7-methoxy-4-quinolinol (310 mg, 1.23 mmol) and PPh3 (580 mg, 2.21 mmol) were dissolved in dry THF and the temperature was lowered to 0° C. DIAD (435 uL. 2.21 mmol) dissolved in 2 mL dry THF, was added to the mixture during five minutes. After two hours the temperature was raised to room temperature and the solution was stirred overnight. Evaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1) gave 43 (324 mg, 78%).

Workup

  1. customwas lowered to 0° C
  2. additionwas added to the mixture during five minutes
  3. customEvaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1)

Sources & evidence

ORD record
ord-1f2e49f2e14d4746ba744ccbcd5ad068
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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