Hydrochloric Acid → HCID 22123604, compound

HRID 1859325Notes

Reaction equation

COC[O:4][C:5]1[CH:43]=[CH:42][C:8]2[CH:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20]COC)=[CH:16][CH:15]=3)([CH3:13])[CH2:11][O:12][C:7]=2[CH:6]=1.Cl.O>CO>[OH:4][C:5]1[CH:43]=[CH:42][C:8]2[CH:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)([CH3:13])[CH2:11][O:12][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(3RS,4RS)-7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[9-(2-piperidinoethylthio)nonyl]-2,3-dihydro-4H-benzopyran (174 mg, 0.28 mmol) and methanol solution of 5N--HCl (1 ml) were dissolved in methanol (10 ml) and then stirred for 5 hours at 40° C. The reaction solution was cooled to room temperature and, after adding water, extracted with ethyl acetate. The organic layer thus separated was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified with flash column chromatography (dichloromethane:ethanol=9:1) to obtain 139 mg (yield: 93%) of the title compound as a pale yellow oil.

Workup

temperatureThe reaction solution was cooled to room temperature
extractionextracted with ethyl acetate
customThe organic layer thus separated
dry with materialwas dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified with flash column chromatography (dichloromethane:ethanol=9:1)

Sources & evidence

ORD record: ord-1814fca5579f47c6a16d2d9733c0997e
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153768

Reaction notes

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