Triphenylphosphine → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl ester

HRID 1443430Notes

Reaction equation

HRID 1443430 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@H:17]1[CH:19]=[CH2:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33](O)=[N:34][C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:36]2)=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH:11]([O:13][C:33]2[C:32]3[C:37](=[CH:38][C:29]([O:28][CH3:27])=[CH:30][CH:31]=3)[N:36]=[C:35]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:34]=2)[CH2:10][CH:9]1[C:14](=[O:26])[NH:15][C:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH:17]1[CH:19]=[CH2:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl esterHCID 178487727HCID 178487727, compound

Product 1

HCID 684230722-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl esterYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 15 (700 mg, 1.9 mmol), 7-methoxy-2-phenyl-quinazolin-4-ol (670 mg, 2.66 mmol) and triphenyl phosphine (1245 mg, 4.75 mmol) were dissolved in THF (50 ml) and cooled to 0° C. Diisopropyl azidocarboxylate (960 mg, 4.75 mmol) was added slowly and the slurry was allowed to reach room temperature. After 12 h, the solvent was removed under reduced pressure and the residue taken up in ether and filtrated. Purification by column chromatography (SiO2; 1% methanol in dichloromethane) gave the pure title compound (778 mg, 68%). MS (M+H)+ 603.

Workup

  1. customto reach room temperature
  2. customthe solvent was removed under reduced pressure
  3. filtrationfiltrated
  4. customPurification by column chromatography (SiO2; 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-55272f3cb3434ae0ba10f8b5a220e061
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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