Methanol → HCID 58387991, compound

HRID 2080263Notes

Reaction equation

HRID 2080263 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12](=S)OCC)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O:17]([C:24]1[CH:25]=[C:26]([CH:39]=[CH:40][CH:41]=1)COS(C1C=CC(C)=CC=1)(=O)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.CC(C)([O-])C.[K+]>O1CCCC1>[O:17]([C:24]1[CH:25]=[C:26]([CH:39]=[CH:40][CH:41]=1)[CH2:12][S:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 13643703HCID 13643703, compoundHCID 23665647Potassium tert-butoxideHCID 58388007HCID 58388007, compound

Product 1

HCID 58387991HCID 58387991, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dithiocarbonic acid O-ethyl ester S-quinolin-6-yl ester described in Preparation Example W-1 (50 mg, 0.201 mmol), toluene-4-sulfonic acid 3-phenoxybenzyl ester (110 mg, 0.313 mmol) and methanol (1 ml) in tetrahydrofuran (5 ml) was added potassium tert-butoxide (135 mg, 1.20 mmol) under nitrogen atmosphere, which was then stirred at room temperature for 24 hours. This reaction solution was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1), and the title compound (39 mg, 0.114 mmol, 57%) was obtained as a yellow oil.

Workup

  1. customThis reaction solution was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-28bda0fb55e54bc8b73bee298ea17ede
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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