Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=C[C:21](C(O)=O)=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49][CH3:50])CC)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:21]([C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:23]=[CH:50][C:49]=1[NH2:46])=[O:34])([CH3:54])([CH3:53])[CH3:52]Participants
Procedure
A mixture of 4-[3-(2-benzyloxyphenyl)propyl]benzene carboxylic acid (8.39 g), diphenylphosphoryl azide (5.74 ml) and triethylamine (7.1 ml) in t-butanol (80 ml) was heated under reflux in an argon atmosphere for 16 hours. The reaction mixture was evaporated to dryness and the residue partitoned between ethyl acetate and water. The ethyl acetate extract was washed once each with 2N HCl, water, saturated aqueous sodium bicarbonate solution and brine (20 ml each time) and dried (MgSO4). The solvent was evaporated and the residue subjected to flash chromatography eluted with a mixture of dichloromethane:hexane (1:1 v/v) to give N t-butyloxycarbonyl-4-{3-(2-benzyloxyphenyl)propyl]benzene-amine 7.69 g m.p. 86°-8° C. which was used directly in the next step.
Workup
- temperaturewas heated
- temperatureunder reflux in an argon atmosphere for 16 hours
- customThe reaction mixture was evaporated to dryness
- extractionThe ethyl acetate extract
- washwas washed once each with 2N HCl, water, saturated aqueous sodium bicarbonate solution and brine (20 ml each time)
- dry with materialdried (MgSO4)
- customThe solvent was evaporated
- washeluted with a mixture of dichloromethane:hexane (1:1 v/v)
Sources & evidence
- ORD record
- ord-28b7cf6826bf4a3c962538dcb0786d6e
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811459
Linked notes
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