Methyl iodide → 4-(4-Dimethylcarbamoyl-phenoxy)-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:19]=[C:18]([O:20]CC2C=CC=CC=2)[C:11]2[CH2:12][CH:13]([CH2:15][O:16][CH3:17])[O:14][C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(C1C=C(O[C:47]2[CH:52]=[CH:51][C:50]([C:53](=[O:57])[N:54]([CH3:56])[CH3:55])=[CH:49][CH:48]=2)C2CC(CO)OC=2C=1)=O)(C)(C)C.CI>>[C:1]([O:5][C:6]([C:8]1[CH:19]=[C:18]([O:20][C:47]2[CH:52]=[CH:51][C:50]([C:53](=[O:57])[N:54]([CH3:55])[CH3:56])=[CH:49][CH:48]=2)[C:11]2[CH2:12][CH:13]([CH2:15][O:16][CH3:17])[O:14][C:10]=2[CH:9]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner as described for Intermediate 204b, from 4-(4-dimethylcarbamoyl-phenoxy)-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (211a) and methyl iodide. 1H NMR (400 MHz, CDCl3) δ 7.40-7.43 (m, 2 H) 7.24 (d, J=1.26 Hz, 1 H) 7.17 (d, J=1.26 Hz, 1 H) 6.92-7.01 (m, 2 H) 4.92-5.05 (m, 1 H) 3.51-3.59 (m, 2 H) 3.41 (s, 3 H) 2.99-3.15 (m, 7 H) 2.81-2.90 (m, 1 H) 1.54 (s, 9 H); LCMS for C24H29NO6 m/z 428.20 (M+H+).
Sources & evidence
- ORD record
- ord-3ec9a4653f014a458e215a92b6d89db0
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119624B2
Reaction notes
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