Phenol → HCID 131733440, compound

HRID 2277055Notes

Reaction equation

HRID 2277055 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.[OH:29][C@@H:30]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43](O)[CH:42]=1)[CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]>>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH2:17][CH:13]1[CH2:12][O:11][C:43]1[CH:42]=[C:41]([C@H:30]([OH:29])[CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])[CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 14099474(2,3-Dihydro-1-benzofuran-2-yl)methyl 4-methylbenzene-1-sulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 131733440HCID 131733440, compound

Procedure

Reaction between ((2,3-dihydrobenzofuran-2-yl)methyl 4-methylbenzenesulfonate and phenol (7, Intermediate I) following the method used in Example 12 gave tert-butyl ((3R)-3-(3-((2,3-dihydrobenzofuran-2-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate as a white solid. Yield (65%); 1H NMR (400 MHz, CDCl3): δ 7.24-7.18 (m, 2H), 7.12 (t, J=8 Hz, 1H), 6.94 (t, J=8.4 Hz, 2H), 6.88-6.81 (m, 3H), 5.16-5.13 (m, 1H), 4.87 (s, 1H), 4.71 (s, 1H), 4.20 (dd, J=10.0, 6.8 Hz m, 1H), 4.10 (dd, J=6.0, 4.8 Hz, 1H), 3.41 (s, 1H), 3.39-3.35 (m, 1H), 3.25 (s, 1H), 3.17-3.11 (m, 2H), 1.85-1.80 (m, 2H), 1.45 (s, 9H); MS: m/z 400 [M+H]+.

Sources & evidence

ORD record
ord-033cc00a2269461bbc5626599380cb90
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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