Diisopropylethylamine → (5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione

HRID 1669655ノート

反応式

HRID 1669655 の反応式
Cl.[CH3:2][Si:3]([C:6]#[C:7][C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=1)([CH3:5])[CH3:4].[CH3:14][C@@:15]1([CH2:22][S:23](Cl)(=[O:25])=[O:24])[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:14][C@:15]1([CH2:22][S:23]([N:11]2[CH2:10][CH:9]=[C:8]([C:7]#[C:6][Si:3]([CH3:4])([CH3:5])[CH3:2])[CH2:13][CH2:12]2)(=[O:25])=[O:24])[NH:16][C:17](=[O:21])[NH:18][C:19]1=[O:20]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 673510094-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochloride

生成物 1

HCID 67351634(5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione収率 91.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

4-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochloride (3.43 g, 15.9 mmol) was stirred in THF (100 mL) with [(4S)-4-methyl-2,5-dioxoimidazolidin -4-yl]methanesulfonyl chloride (3.39 g, 15 mmol) and cooled in an ice salt bath (temperature about −10° C.). N-Ethyldiisopropylamine (5.13 mL, 30 mmol) in THF (100 mL) was added dropwise over 2 hours and the mixture stirred a further 2 hours. The reaction mixture was washed with water, the aqueous layer extracted into EtOAc (×2), the organic phases combined, washed with 2M HCl (×2), saturated bicarbonate solution (x2), followed by brine, dried (sodium sulphate) and evaporated to give the crude product (5.06 g). This was used without further purification.

後処理

  1. washThe reaction mixture was washed with water
  2. extractionthe aqueous layer extracted into EtOAc (×2)
  3. washwashed with 2M HCl (×2), saturated bicarbonate solution (x2)
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

出典と根拠

ORDレコード
ord-8e726a72f8194378abc4fc85de84dc91
出典データセット
uspto-grants-2011_08
特許番号
US07989620B2

反応ノート

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