Isopropylamine → N-[7-(isopropylamino-methyl)-chroman-4-yl]-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

HRID 32056

반응식

HRID 32056 반응식
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.CS(OS(C)(=O)=O)(=O)=O.[CH:56]([NH2:59])([CH3:58])[CH3:57]>C1COCC1.C(Cl)(Cl)Cl>[CH:56]([NH:59][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)([CH3:58])[CH3:57]

참가 물질

7

반응물 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 68932544N-(7-hydroxymethyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

생성물 1

HCID 68928313N-[7-(isopropylamino-methyl)-chroman-4-yl]-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

N-(7-Hydroxymethyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Step A) (0.050 g, 0.010 mmol) and DIEA (0.038 g, 0.030 mmol) were dissolved in THF (1.5 mL). The solution was cooled to 0° C. and methanesulfonic anhydride (0.023 g, 0.014 mmol) was added. After the reaction was stirred for 3.5 h, isopropylamine (0.14 g, 2.3 mmol) was added and the solution was stirred at RT overnight. The reaction was diluted with CHCl3 and washed with brine. The aqueous phase was extracted once with CHCl3. The organic phases were combined, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (silica, 0.2% TEA in acetone) to provide the title compound. MS (ESI) m/z 558 (M+H)+.

후처리

  1. stirringthe solution was stirred at RT overnight
  2. washwashed with brine
  3. extractionThe aqueous phase was extracted once with CHCl3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue which
  8. customwas purified by column chromatography (silica, 0.2% TEA in acetone)

출처 및 근거

ORD 기록
ord-5e3421b9ffec4c83ab2a6feeab9ea2e4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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