Phenol → HCID 131733441, compound

HRID 2277056Notes

Reaction equation

HRID 2277056 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.[OH:25][C@@H:26]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39](O)[CH:38]=1)[CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>CCOC(C)=O>[OH:25][C@@H:26]([C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)[CH:42]=1)[CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 996PhenolHCID 4522871(Tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 131733441HCID 131733441, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl ((3R)-3-hydroxy-3-(3-((tetrahydrofuran-2-yl)methoxy)phenyl)propyl)-carbamate was prepared by the reaction between rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate and phenol (7, Intermediate I) at +100° C. following the method used in Example 12 with the following exception. After the reaction was complete (as judged by TLC), the reaction mixture was diluted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (EtOAc:hexane 10-40% gradient) gave the product as an off-white semi-solid. Yield (0.36 g, 66%); 1H NMR (400 MHz, CDCl3): δ 7.23 (t, J=8.0 Hz, 1H), 6.95 (s, 1H), 6.91 (d, J=8.0 Hz, 1H), 6.82 (d, 1H), 4.88 (bs, 1H), 4.71 (bs, 1H), 4.28-4.25 (m, 1H), 3.96-3.90 (m, 3H), 3.85-3.82 (m, 1H), 3.49 (bs, 1H), 3.19-3.13 (m, 2H), 1.97-1.92 (m, 2H), 1.83-1.74 (m, 3H), 1.60 (s, 1H), 1.45 (s, 9H); MS: m/z 352.8 [M+H]+.

Workup

  1. dry with materialdried over anhydrous Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash chromatography (EtOAc:hexane 10-40% gradient)

Sources & evidence

ORD record
ord-57e1520827f84397ab1fd200544d2d39
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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