N-(2,2-dimethyl-1(S)-(N-methylcarbamoyl)-propyl)-2-(2-biphenyl-4-yl-furan-5-yl)-acetamide → N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propy]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:43])[C@@H:7](C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)CC(NN1[C@@H](CC2C=CC=CC=2)COC1(C)C)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:44][C:45]([CH3:73])([CH3:72])[C@H:46]([NH:51][C:52](=[O:71])[CH2:53][C:54]1[O:58][C:57]([C:59]2[CH:64]=[CH:63][C:62]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:61][CH:60]=2)=[CH:56][CH:55]=1)[C:47](=[O:50])[NH:48][CH3:49].C([Li])CCC>>[C:1]([O:5][C:6](=[O:43])[CH2:7][CH:53]([C:54]1[O:58][C:57]([C:59]2[CH:60]=[CH:61][C:62]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:63][CH:64]=2)=[CH:56][CH:55]=1)[C:52]([NH:51][C@H:46]([C:47](=[O:50])[NH:48][CH3:49])[C:45]([CH3:73])([CH3:72])[CH3:44])=[O:71])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Procedure
According to the procedure described in Example 13 for the preparation of N-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2(R)-(biphenyl-4-yl-1H-pyrrol-3-yl)succinamic acid t-butyl ester, but N-(2,2-dimethyl-1(S)-(N-methylcarbamoyl)-propyl)-2-(2-biphenyl-4-yl-furan-5-yl)-acetamide was instead deprotonated with n-butyllithium (3.1 equiv) and alkylated to furnish 17 mg(7%) of N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl ester as an amorphous solid. 1H NMR: δ 7.70 (d, 2H, J=8.1 Hz), 7.62-7.59 (m, 4H), 7.45 (t, 2H, J=7.5 Hz), 7.35 (t, 1H, J=7.4 Hz), 6.63 (d, 1H, J=3.3 Hz), 6.50 (d, 1H, J=9.6 Hz), 6.33 (d, 1H, J=3.3 Hz), 5.09 (bm, 1H), 4.19-4.10 (m, 2H), 3.15 (dd, 1H, J=8.5, 16.6 Hz), 2.86-2.73 (m, 4H), 1.41 (s, 9H), 0.89 (s, 9H). HRMS: Calculated for C31H39N2O5 (M+H+): 519.2859. Found: 519.2865.
Sources & evidence
- ORD record
- ord-7fcc0831e1434706b5a4e3044674104c
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495699B2
Reaction notes
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