1-Hydroxybenzotriazole hydrate → 1-t-butoxycarbonyl-4-{1-(4-fluorophenyl)-2-[4-(4-naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-3,6-dihydro-2H-pyridine

HRID 497345ノート

反応式

HRID 497345 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([CH:14]([C:22]([OH:24])=O)[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.[C:27]1([CH2:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=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][CH:12]=[C:11]([CH:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:22]([N:44]2[CH2:43][CH2:42][N:41]([CH2:40][CH2:39][CH2:38][CH2:37][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)[CH2:46][CH2:45]2)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 223186591-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridineHCID 223186681-(4-Naphthalen-1-yl-butyl)piperazine dihydrochlorideHCID 574299851-(3,3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

生成物 1

HCID 223186421-t-butoxycarbonyl-4-{1-(4-fluorophenyl)-2-[4-(4-naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-3,6-dihydro-2H-pyridine収率 61.9%

試薬・触媒・溶媒 3

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

実験手順

0.49 g of 1-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine obtained in Example 11(2) was dissolved in 5 ml of dimethylformamide, and 0.55 g of 1-(4-naphthalen-1-yl-butyl)piperazine dihydrochloride, 0.34 g of 1-(3,3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.34 g of 1-hydroxybenzotriazole monohydrate and 0.5 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=2:1) to give 0.53 g of 1-t-butoxycarbonyl-4-{1-(4-fluorophenyl)-2-[4-(4-naphthalen-1-yl-butyl)piperazin-1-yl]-2-oxoethyl}-3,6-dihydro-2H-pyridine 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=2:1)

出典と根拠

ORDレコード
ord-e3177b7d7f7149a8810e6b29161e8cab
出典データセット
uspto-grants-2005_09
特許番号
US06949552B2

反応ノート

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