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1-Hydroxybenzotriazole hydrate → 1-t-Butoxycarbonyl-4-(1-(4-fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine

HRID 497338
ノート
印刷プレビュー

反応式

HRID 497338 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:22](O)=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:27][O:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]=1[CH2:39][CH2:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.Cl.CNC(NC)CCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:22]([N:46]2[CH2:45][CH2:44][N:43]([CH2:42][CH2:41][CH2:40][CH2:39][C:30]3[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:37]=[CH:38][C:29]=3[O:28][CH3:27])[CH2:48][CH2:47]2)=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 223186521-[4-(2-Methoxynaphthalen-1-yl)butyl]piperazine dihydrochlorideHCID 223186671-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]piperidineHCID 574299851-(3,3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

生成物 1

HCID 223186381-t-Butoxycarbonyl-4-(1-(4-fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine
収率 72.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2.2 g of 1-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]piperidine was dissolved in 20 ml of dimethylformamide, and 2.0 g of 1-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine dihydrochloride, 1.9 g of 1-(3,3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1.9 g of 1-hydroxybenzotriazole monohydrate and 3.5 ml of triethylamine were added, followed by stirring at room temperature overnight. The reaction solution was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=3:1) to give 2.4 g of 1-t-butoxycarbonyl-4-(1-(4-fluorophenyl)-2-{4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin-1-yl}-2-oxoethyl)piperidine as an oil.

後処理

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customAfter removal of the drying agent
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-fedcccc921904bc88708d4e6dafcac37
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949552B2

反応ノート

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