1-{[1-(N'-tert-Butoxycarbonyl-N-hept-6-enyl-hydrazinocarbonyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester → HCID 68578578, compound

HRID 1822472Notes

Reaction equation

HRID 1822472 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][N:15]2[C:38]([N:40]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]C=C)[NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:39])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]>ClCCl.C(OC(N1CC(OC2C3C(=CC(OC)=CC=3)N=C(C3C=CC=CC=3)C=2)CC1C(=O)NC1(C(OCC)=O)CC1C=C)=O)(C)(C)C>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:10][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][N:40]([NH:41][C:42]([O:44][C:45]([CH3:47])([CH3:48])[CH3:46])=[O:43])[C:38](=[O:39])[N:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 685786161-{[1-(N'-tert-Butoxycarbonyl-N-hept-6-enyl-hydrazinocarbonyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68578578HCID 68578578, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 20765329HCID 20765329, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 120 (200 mg, 0.26 mmol) was dissolved in degassed dichloromethane (30 ml). Hoveyda-Grubbs catalyst 11 generation (16 mg, 0.026 mmol) was then added and the mixture was refluxed under argon atmosphere overnight. The solvent was then evaporated and the crude product was purified by silica chromatography (1% methanol in ether) which gave 39 mg (20%) of the title product. MS (M+H+) 728.2

Workup

  1. temperaturethe mixture was refluxed under argon atmosphere overnight
  2. customThe solvent was then evaporated
  3. customthe crude product was purified by silica chromatography (1% methanol in ether) which

Sources & evidence

ORD record
ord-386ab719487c441192c5014749c9e0fe
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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