Water → 6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

HRID 1043372노트

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HRID 1043372 반응식
N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[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>[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:35][N:7]([CH2:35][C:31]1[N:30]([CH3:29])[CH:47]=[CH:49][N:32]=1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:8]([OH:10])=[O:9]

참가 물질

6

반응물 4

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

생성물 1

HCID 674296096-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid수율 160%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

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)-2-4(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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-822e752198f54147a815e25fff1d54e9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08562945B2

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