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Diisopropylethylamine → tert-Butyl ((1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)carbamate

HRID 969579
ノート
印刷プレビュー

反応式

HRID 969579 の反応式
Cl.Cl.[F:3][C:4]([F:16])([F:15])[C:5]1[CH:6]=[N:7][C:8]2[CH2:9][CH2:10][NH:11][CH2:12][C:13]=2[CH:14]=1.[C:17]([O:21][C:22]([NH:24][C@@H:25]1[CH2:29][CH2:28][C@:27]([CH:33]([CH3:35])[CH3:34])([C:30](O)=[O:31])[CH2:26]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH:33]([C@:27]1([C:30]([N:11]2[CH2:10][CH2:9][C:8]3[N:7]=[CH:6][C:5]([C:4]([F:15])([F:3])[F:16])=[CH:14][C:13]=3[CH2:12]2)=[O:31])[CH2:28][CH2:29][C@@H:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:26]1)([CH3:35])[CH3:34]
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 81531DiisopropylethylamineHCID 60122293(1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acidHCID 669114653-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine--hydrogen chloride (1/2)

生成物 1

HCID 60122330tert-Butyl ((1R,3S)-3-Isopropyl-3-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)carbamate収率 114.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine dihydrochloride (159 mg, 0.574 mmol) of Step A-1, (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (0.21 g, 0.79 mmol) of Step A-4 in Example 1 in dichloromethane (10 mL) were added 4-dimethylaminopyridine (38 mg, 0.32 mmol) and diisopropylethylamine (180 mg, 1.4 mmol) followed by bromotris(pyrrolydino)phophonium hexafluorophosphate (270 mg, 0.57 mmol). After being stirred overnight at room temperature, the solution was diluted with dichloromethane, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography on silica eluting with 30% ethyl acetate in hexanes to give 300 mg of desired product. MS calculated for C23H32F3N3O3: (M+H)+456; found 356.2 (M−Boc+H)+.

後処理

  1. washwashed with saturated NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica eluting with 30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-0f95175d7db54b5d9f8a840d14b56c93
出典データセット
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07307086B2

反応ノート

読み込み中…

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