Diisopropylethylamine → HCID 54455044、化合物

HRID 365433

反応式

HRID 365433 の反応式
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([N:20]([C@H:22]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)[C:23]([OH:25])=O)[CH3:21])=[O:19])([CH3:16])([CH3:15])[CH3:14].ON1C2N=CC=CC=2N=N1.[CH3:47][N:48]([CH3:73])[C:49](=[O:72])[C@@H:50]([NH:59][C:60](=[O:71])[C@H:61]([NH:69][CH3:70])[CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:56](=[O:58])[CH3:57].C(N(C(C)C)C(C)C)C>ClCCl.CN(C)C=O.C(OCC)(=O)C>[C:13]([O:17][C:18](=[O:19])[N:20]([C@@H:22]([C:23](=[O:25])[N:69]([C@@H:61]([C:60](=[O:71])[NH:59][C@H:50]([C:49](=[O:72])[N:48]([CH3:47])[CH3:73])[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:56](=[O:58])[CH3:57])[CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[CH3:70])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=1)[CH3:21])([CH3:15])([CH3:14])[CH3:16]

参加物

9

反応物 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10065151(2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acidHCID 54227586HCID 54227586、化合物

生成物 1

HCID 54455044HCID 54455044、化合物収率 73.6%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (594 mg, 3.1 mmol) was added at 0° C. to a solution of (2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-(2-naphthyl)propionic acid (1.02 g, 3.1 mmol) and 1-hydroxy-7-azabenzotriazole (422 mg, 3.1 mmol) in dichloromethane (10 ml) and N,N-dimethylformamide (5 ml). The reaction mixture was stirred for 20 min at 0° C. A solution of the hydrochloride salt of crude (2S)-6-acetylamino-2-(((2R)-2-(methylamino)-3-phenylpropionyl)amino)hexanoic acid dimethylamide (1.28 g, 3.1 mmol) in dichloromethane (20 ml)and N,N-dimethylformamide (10 ml) and ethyidiisopropylamine (1.59 ml, 9.3 mmol) were added subsequently. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was diluted with ethyl acetate (200 ml) and washed with a 10% aqueous sodium hydrogen sulfate solution (150 ml). The aqueous solution was extracted wtih ethyl acetate (3×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (120 g), usin dichloromethane/methanol (10:1) as eluent, to give 1.57 g of N-((1R)-1-{N-[(1R)-1-((1S)-5-(acetylamino)-1-(dimethylcarbamoyl)pentylcarbamoyl)-2-phenylethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butyl ester.

後処理

  1. stirringThe reaction mixture was stirred for 16 h, while it
  2. temperaturewas warming up to room temperature
  3. washwashed with a 10% aqueous sodium hydrogen sulfate solution (150 ml)
  4. extractionThe aqueous solution was extracted wtih ethyl acetate (3×100 ml)
  5. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (200 ml)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe crude product was purified by flash chromatography on silica (120 g)

出典と根拠

ORDレコード
ord-5d25af5a96eb4abeab81206a9f747040
出典データセット
uspto-grants-2000_10
特許番号
US06127341

関連ノート

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