Diisopropylethylamine → 1,3,7,8-Tetrahydro-8-[[[(4-Methylphenyl)Sulfonyl]Oxy]Methyl]-2H-[1,4]Dioxino[2,3-e]Benzimidazol-2-One

HRID 982678

反応式

HRID 982678 の反応式
Cl.Cl.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][C@@H:15]2[O:20][C:19]3[C:21]([NH2:26])=[C:22]([NH2:25])[CH:23]=[CH:24][C:18]=3[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:27](C1NC=CN=1)(C1NC=CN=1)=[O:28].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][CH2:14][CH:15]2[O:20][C:19]3[C:21]4[NH:26][C:27](=[O:28])[NH:25][C:22]=4[CH:23]=[CH:24][C:18]=3[O:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86586513[(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride

生成物 1

HCID 102929161,3,7,8-Tetrahydro-8-[[[(4-Methylphenyl)Sulfonyl]Oxy]Methyl]-2H-[1,4]Dioxino[2,3-e]Benzimidazol-2-One

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.30 g (0.71 mmole) of [(2R)-7,8-diamino-2,3-dihydro-1,4 benzodioxin-2-yl]methyl 4-methylbenzenesulfonate dihydrochloride in 50 mL of methylene chloride was added 0.50 g (3.0 mmole) of carbonyl diimidazole and 0.65 g (5.0 mmole) of diisopropylethylamine. The reaction mixture was stirred under nitrogen for 15 hours. The mixture was then concentrated in vacuum and 250 mL of ethyl acetate added. This solution was washed with 250 mL portions each of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on 25 g of silica gel, using a gradient elution commencing with chloroform and ending with 3% methanol in chloroform. The product fractions were combined and evaporated in vacuum to give 0.21 g of the (R)-enantiomer of the title compound as an off-white solid, m.p. 202-204° C.

後処理

  1. concentrationThe mixture was then concentrated in vacuum and 250 mL of ethyl acetate
  2. additionadded
  3. washThis solution was washed with 250 mL portions each of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on 25 g of silica gel
  8. customevaporated in vacuum

出典と根拠

ORDレコード
ord-bb2d7e9e9298490f94fa8d872f12e7c3
出典データセット
uspto-grants-2005_03
特許番号
US06861434B2

関連ノート

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