Triethylamine → HCID 22033375, compound

HRID 1792340Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:39]=[CH:38][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=3)[S:16][CH2:15][C:14]2([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH3:27])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49].[Cl-].[NH4+]>C(Cl)Cl>[CH3:47][S:48]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:39]=[CH:38][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=3)[S:16][CH2:15][C:14]2([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH3:27])=[CH:7][CH:6]=1)(=[O:50])=[O:49]

Participants

Conditions

Temperature: 0 °C

Procedure

4-{3-[4-(2-Hydroxyethoxy)phenoxy]propyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (7) prepared in Step 5 (45.6 mg, 0.082 mmol) was dissolved in CH2Cl2 (0.4 ml), which was then cooled down to 0° C. Triethylamine (23 μl, 0.17 mmol) and methanesulfonylchloride (16 μl, 0.21 mmol) were added thereto, and the mixture was stirred for 30 minutes. Saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and subjected to silica gel column chromatography to give 4-{3-[4-(2-methanesulfonyloxyethoxy)phenoxy]propyl}-7-methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methylthiochroman (8) (49.2 mg, yield 95%) as a colorless oily substance.

Workup

extractionthe resulting mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-e6f4b44fa9634597a85ac14df68e2893
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074819B2

Reaction notes

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