tert-Butanol → 3-tert-butyloxycarbonylamino-4-(2-methylphenyl)-7,8-dihydro-6H-cyclopenta[g][1]benzopyran-2-one
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]2[CH:14]=[C:15]3[CH2:20][CH2:19][CH2:18][C:16]3=[CH:17][C:12]=2[O:11][C:10](=[O:21])[C:9]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[C:49]([OH:53])([CH3:52])([CH3:51])[CH3:50]>>[C:49]([O:53][C:47]([NH:44][C:9]1[C:10](=[O:21])[O:11][C:12]2[CH:17]=[C:16]3[CH2:18][CH2:19][CH2:20][C:15]3=[CH:14][C:13]=2[C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:32])([CH3:52])([CH3:51])[CH3:50]Participants
Reactant 4
Product 1
Procedure
To a solution of 4-(2-methylphenyl)-2-oxo-2,6,7,8tetrahydrocyclopenta [g][1]benzopyran-3-carboxylic acid (2.5 g) and diphenyl phosphoryl azide (DPPA, 2.58 g) in tert-butanol (25 ml) was added triethylamine (1.1 ml) dropwise and the mixture was stirred at room temperature for 30 minutes and, then, refluxed for 4 hours. The solvent was distilled off and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and distilled to remove the solvent, whereby 3-tert-butyloxycarbonylamino-4-(2-methylphenyl)-7,8-dihydro-6H-cyclopenta[g] [1]benzopyran-2-one was obtained as oil. The oil was crystallized from hexane (2.95 g, 96.7%). Recrystallization from ethanol-hexane gave colorless prisms, m.p. 154°-155° C.
Workup
- temperaturerefluxed for 4 hours
- distillationThe solvent was distilled off
- additionthe residue was diluted with water
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried (MgSO4)
- distillationdistilled
- customto remove the solvent
Sources & evidence
- ORD record
- ord-717fbb7035884a4bac0037e5a542223b
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05418239
Reaction notes
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