Phenol → (R)-tert-butyl (3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate

HRID 2277048Notes

Reaction equation

HRID 2277048 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15][CH2:14]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.[OH:28][C@@H:29]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42](O)[CH:41]=1)[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>>[O:20]=[S:16]1(=[O:19])[CH2:15][CH2:14][CH:13]([CH2:12][O:11][C:42]2[CH:41]=[C:40]([C@H:29]([OH:28])[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH:45]=[CH:44][CH:43]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 996PhenolHCID 57431037(1,1-Dioxidotetrahydrothiopyran-4-yl)methyl 4-MethylbenzenesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 131733436(R)-tert-butyl (3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate

Procedure

Reaction between (1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl 4-methylbenzenesulfonate and phenol (7, Intermediate I) following the method used in Example 7 gave (R)-tert-butyl (3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate as colorless oil. Yield (58%); 1H NMR (400 MHz, DMSO-d6): δ 7.20 (t, J=8.0 Hz, 1H), 6.87 (d, J=8.0 Hz, 2H), 6.78 (d, J=4.0 Hz, 1H), 5.19 (d, J=4.4 Hz, 1H), 4.51-4.49 (bs, 1H), 3.87-3.85 (d, J=8.0 Hz, 1H), 3.22-3.15 (m, 2H), 3.08-3.05 (m, 2H), 2.96-2.94 (m, 2H), 2.15-2.11 (m, 3H), 1.79-1.74 (m, 2H), 1.67-1.65 (m, 2H), 1.36 (s, 9H).

Sources & evidence

ORD record
ord-83579a14546c4307a2dc2fab2e20622b
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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