Water → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

HRID 56317

反応式

HRID 56317 の反応式
[NH:1]([C:11]([O:13][CH2:14][CH:15]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].Cl.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O.[BH-](O[C:47]([CH3:49])=O)(OC(C)=O)OC(C)=O.[Na+].O>ClCCCl>[CH:17]1[C:16]2[CH:15]([CH2:14][O:13][C:11]([NH:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:35][C:31]3[N:30]([CH3:29])[CH:47]=[CH:49][N:32]=3)[CH2:35][C:31]3[N:30]([CH3:29])[CH:34]=[CH:33][N:32]=3)[C:8]([OH:10])=[O:9])=[O:12])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11858928(2S)-6-amino-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid hydrochloride

生成物 1

HCID 12985318(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid収率 92%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

A solution of Fmoc-Lys-OH.HCl (1.822 g, 4.5 mmol) and 1-methyl-1H-imidazole-2-carbaldehyde (1.10 g, 10 mmol) in DCE (50 mL) was stirred at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM, the organic layer dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid (2.30 g, 92%). MS (ESI), 557 (M+H)+.

後処理

  1. extractionThe reaction mixture was extracted with DCM
  2. customthe organic layer dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-0cfc7421e0b44442bf0f9cbd605c1734
出典データセット
uspto-grants-2016_09
特許番号
US09433594B2

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