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Triethylamine → HCID 59677014, 화합물

HRID 459561
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HRID 459561 반응식
Cl.[CH3:2][O:3][CH:4]1[CH2:8][C@@H:7]([NH2:9])[C@H:6]([NH2:10])[CH2:5]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29])=[CH:22]2>CN(C)C=O>[CH3:2][O:3][CH:4]1[CH2:8][C@@H:7]([NH:9][C:28]([C:23]2[NH:24][C:25]3[C:21]([CH:22]=2)=[CH:20][C:19]([Cl:18])=[CH:27][CH:26]=3)=[O:29])[C@H:6]([NH2:10])[CH2:5]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 17842415p-Nitrophenyl 5-chloroindole-2-carboxylateHCID 57481677HCID 57481677, 화합물

생성물 1

HCID 59677014HCID 59677014, 화합물수율 34.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(1R*,2R*)-4-Methoxy-1,2-cyclopentanediamine hydrochloride (470 mg) was suspended in N,N-dimethylformamide (5 ml), and triethylamine (0.966 ml) and p-nitrophenyl 5-chloroindole-2-carboxylate (805 mg) were added to stir the mixture at room temperature for 4 days. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate and dichloromethane were added to the residue to conduct liquid separation. The resultant organic layers was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:9) to obtain (1R*,2R*)-4-methoxy-N1-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclopentanediamine (mixture of stereoisomers at 4-position) (268 mg) as yellow powder.

후처리

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate and dichloromethane were added to the residue
  3. customliquid separation
  4. dry with materialThe resultant organic layers was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:9)

출처 및 근거

ORD 기록
ord-35b8944c6d7249aa9f3817e160dafff9
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07192968B2

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