Triphenylphosphine → 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

HRID 643833Notes

Reaction equation

HRID 643833 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]([C:10](=[O:24])[NH:11][C@:12]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][C@H:13]2[CH:15]=[CH2:16])[CH2:8][CH:7]([OH:25])[CH:6]=1)=[O:4].[CH3:26][O:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32](O)=[CH:33][C:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:35]2)=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:9]([C:10](=[O:24])[NH:11][C@:12]2([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:14][C@H:13]2[CH:15]=[CH2:16])[CH2:8][CH:7]([O:25][C:32]2[C:31]3[C:36](=[CH:37][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[N:35]=[C:34]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:33]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 592041965-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl esterHCID 178487676HCID 178487676, compound

Product 1

HCID 592041875-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 29 (41 mg, 116 mmol) in dry THF, 7-methoxy-2-phenyl-quinolin-4-ol (150 mmol) and triphenylphosphine (150 mmol) were added. Then DIAD (160 mmol) was dissolved in THF (2 mL) and added dropwise to the solution. After one hour the mixture was concentrated and purified using flash chromatography (toluene/ethyl acetate 3:1). This gave the title compound as a yellow oil.

Workup

  1. additionadded dropwise to the solution
  2. concentrationAfter one hour the mixture was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-ee34652d40114054a7c99e44176289e1
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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