HCID 22033347, compound → HCID 22033036, compound

HRID 1792375Notes

Reaction equation

HRID 1792375 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][O:38][CH2:39][C:40]([F:43])([F:42])[F:41])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1>Cl.CO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][O:38][CH2:39][C:40]([F:43])([F:42])[F:41])[C:10]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 22033347HCID 22033347, compound

Product 1

HCID 22033036HCID 22033036, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

(3RS,4RS)-7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{9-[2-(2,2,2-trifluoroethoxy)ethylthio]nonyl}thiochroman (136 mg, 0.211 mmol) was dissolved in 10% HCl/MeOH (20 ml) and the mixture was stirred at room temperature for 1 day. After the reaction was completed, the mixture was concentrated, and silica gel column chromatography (n-hexane/ethyl acetate=5/1) gave (3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{9-[2-(2,2,2-trifluoroethoxy)ethylthio}nonyl}thiochroman (100 mg, 85%)

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-f8c7a6864281443d9dd32c687151bd2f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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