Triethylamine → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N,2-dimethylalanine

HRID 74824노트

반응식

HRID 74824 반응식
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[CH3:16][NH:17][C:18]([CH3:23])([C:20]([OH:22])=[O:21])[CH3:19].C(N(CC)CC)C>ClCCl>[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:17]([CH3:16])[C:18]([CH3:23])([C:20]([OH:22])=[O:21])[CH3:19])=[O:14]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 75725alpha-(Methylamino)isobutyric acidHCID 114247166-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chloride

생성물 1

HCID 86685780N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N,2-dimethylalanine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirring solution of #248 (600 mg, 2.61 mM) in 10 mL of dichloromethane, N,2-dimethylalanine (306 mg, 2.61 mM) was added followed by triethylamine (1.09 mL, 7.84 mM). The reaction was allowed to stir at room temperature for three hours. Dichloromethane was added to the reaction and the organic layer was washed three times with water and two times with brine. The organic layer was separated and then dried over sodium sulfate before being concentrated in vacuo. The crude residue was purified by silica chromatography (0-30% methanol in dichloromethane) on silica which had been previously neutralized with triethylamine yielding a white solid #249 (127 mg, 16%). LC-MS (Protocol Q): m/z 309.0 [M−H−], retention time=0.96 minutes.

후처리

  1. washthe organic layer was washed three times with water and two times with brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationbefore being concentrated in vacuo
  5. customThe crude residue was purified by silica chromatography (0-30% methanol in dichloromethane) on silica which

출처 및 근거

ORD 기록
ord-74efc5e1084542d7b9b15aab9a360501
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828401B2

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