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Methanesulfonyl chloride → 2-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate

HRID 2278780
ノート
印刷プレビュー

反応式

HRID 2278780 の反応式
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:26]=[C:25]([CH3:27])[C:20]([O:21][CH2:22][CH2:23][OH:24])=[C:19]([CH2:28][CH3:29])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:30][CH3:31])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C1COCC1.CC(=O)OCC>[CH3:41][S:42]([O:24][CH2:23][CH2:22][O:21][C:20]1[C:25]([CH3:27])=[CH:26][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[C:8]([O:30][CH3:31])[N:7]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:11]=3)[O:16][N:15]=2)=[CH:18][C:19]=1[CH2:28][CH3:29])(=[O:44])=[O:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 705581362-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethanol

生成物 1

HCID 867020182-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate収率 96.8%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethanol (638 mg, 1.51 mmol) in THF, DIPEA (389 mg, 3.01 mmol) is added. The mixture is cooled to 0° C. before methanesulfonyl chloride (207 mg, 1.81 mmol) is added. The mixture is stirred at rt for 30 min before it is diluted with EA (100 mL) and washed with sat. aq. NaHCO3 solution (50 mL) and brine (50 mL). The org. extract is dried over MgSO4, filtered and concentrated to give 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate (733 mg) as a yellow oil; LC-MS: tR=1.19 min, [M+H]+=502.05.

後処理

  1. additionis added
  2. washwashed with sat. aq. NaHCO3 solution (50 mL) and brine (50 mL)
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-07fec1059993482b9db5bcd1501c3165
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133179B2

反応ノート

読み込み中…

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