HCID 11234748, compound → HCID 67533783, compound
Reaction equation
CON(C)[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH3:26])=[CH:16][C:15]=3[CH:27]=2)[CH:6]=1.[CH2:30]([Mg]Cl)[CH:31]([CH3:33])[CH3:32]>>[CH3:30][CH:31]([CH3:33])[CH2:32][C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:27]=[CH:15][C:14]3[O:18][C:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH3:26])=[CH:16][C:13]=3[CH:12]=2)[CH:6]=1)=[O:28]Participants
3
Procedure
The product from Example 145 and isobutylmagnesium chloride were processed as described in Example 146, except that after reacting overnight additional isobutylmagnesium chloride (400 mol %) was added and the reaction mixture was stirred for four more hours, to provide the title compound (19% yield). MS (ESI APCI) m/z 390 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.01 (d, 6 H), 1.17 (d, 3 H), 1.37-1.53 (m, 1 H), 1.73-1.86 (m, 2 H), 1.94-2.07 (m, 1 H), 2.20-2.35 (m, 2 H), 2.41-2.59 (m, 2 H), 2.95 (d, 2 H), 2.95-3.14 (m, 2 H), 3.19-3.34 (m, 2 H), 6.62 (s, 1 H), 7.49-7.52 (m, 2 H), 7.57 (dd, 1 H), 7.77 (dd, 1 H), 7.86 (ddd, 1 H), 7.93 (ddd, 1 H), 8.19 (dd, 1 H).
Sources & evidence
- ORD record
- ord-fedf9dc767a241fc8e0431c38f305ad7
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06969730B2
Reaction notes
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