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

HRID 2277049Notes

Reaction equation

HRID 2277049 reaction equation
C[CH:2]1[CH:7]([CH2:8]Br)[CH2:6][CH2:5][CH2:4][S:3]1(=[O:11])=[O:10].C1(O)C=CC=CC=1.[OH:19][C@@H:20]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=1)[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>>[O:11]=[S:3]1(=[O:10])[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][O:37][C:33]2[CH:32]=[C:31]([C@H:20]([OH:19])[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:36]=[CH:35][CH:34]=2)[CH2:2]1

Participants

4

Reactant 3

HCID 996PhenolHCID 90404779methyl 3-(bromomethyl)tetrahydro-2H-thiopyran 1,1-dioxideHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 131733437tert-butyl ((3R)-3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate

Procedure

Reaction between methyl 3-(bromomethyl)tetrahydro-2H-thiopyran 1,1-dioxide and phenol (7, Intermediate I) following the method used in Example 7 gave tert-butyl ((3R)-3-(3-((1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate as a light pink semi-solid. Yield (0.43 g, 65%); 1H NMR (400 MHz, CDCl3): δ 7.24 (t, J=8.0 Hz, 1H), 6.93 (d, J=8.0 Hz, 2H), 6.77-6.75 (m, 1H), 4.86 (bs, 1H), 4.72-4.70 (m, 1H), 3.95-3.92 (m, 1H), 3.90-3.88 (m, 1H), 3.38 (s, 1H), 3.26-3.22 (m, 1H), 3.18-3.13 (m, 1H), 3.06 (d, J=4.0 Hz 1H), 2.97-2.88 (m, 2H), 2.65 (bs, 1H), 2.20-2.04 (m, 2H), 1.99-1.95 (m, 1H), 1.84-1.81 (m, 2H), 1.45 (s, 9H). MS: m/z 414.43 [M+H]+.

Sources & evidence

ORD record
ord-dddcc805b66f4f429bf89c5c3034c9ed
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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