Tyrosol → HCID 59791334, compound

HRID 402215Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(OS(O[CH2:27][CH2:28][O:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=O)=O)=CC=1>CN(C=O)C>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([O:1][CH2:27][CH2:28][O:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 100 ml round bottom flask was charged with 4-hydroxyphenethyl alcohol (1.14 g, 8.2 mmol), cesium carbonate (4.02 g, 12.4 mmol), and tert-butyl 2-(2-{[(4-methylphenoxy)sulfonyl]oxy}ethoxy)-ethylcarbamate (2.96 g, 8.2 mmol) (prepared using standard chemistry). This reaction mixture was slurried with 10 ml of DMF and heated to 60° C. by use of an oil bath. The reaction proceeded for 19 hours at which point was it was cooled and the DMF removed under reduced pressure. Upon adding dichloromethane the reaction mixture was filtered through a plug of celite and then the solvent removed. The resultant solid was dried under high vacuum. A near quantitative yield of product was isolated: 1H NMR (CDCl3) δ 7.11 (d, 2H, Ar), 6.98 (d, 2H, Ar), 4.97 (bs, exchangeable, NH), 4.07 (dd, CH2—O), 3.79 (t, CH2—OH), 3.78 (dd, CH2—O), 3.57 (t, CH2—O), 3.30 (bm, CH2—NH), 2.78 (t, CH2—Ar), 1.82 (bs, exchangeable, OH) 1.41 (s, 9H, CH3). Mass spectrum, m/e Calcd for C17H28NO5+: 326.20 (100%), 327.20 (19.5%). Found: 326.56, 327.57.

Workup

temperaturewas cooled
customthe DMF removed under reduced pressure
additionUpon adding dichloromethane the reaction mixture
filtrationwas filtered through a plug of celite
customthe solvent removed
customThe resultant solid was dried under high vacuum

Sources & evidence

ORD record: ord-3bebb99c6702433e97c8b994a1d2b373
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742086B2

Reaction notes

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