Trifluoroacetic acid → (S)-N-((2S,3S)-1-Acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide

HRID 1486062노트

반응식

HRID 1486062 반응식
[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([N:16](C)[C:17](=O)OC(C)(C)C)[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][C:29]=2[CH:38]2[CH2:40][CH2:39]2)[C:6]2[CH:41]=[CH:42][CH:43]=[CH:44][C:5]1=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([NH:16][CH3:17])[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][C:29]=2[CH:38]2[CH2:39][CH2:40]2)[C:6]2[CH:41]=[CH:42][CH:43]=[CH:44][C:5]1=2)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 118292641tert-butyl(S)-1-((2S,3S)-1-acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

생성물 1

HCID 73425655(S)-N-((2S,3S)-1-Acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a rt solution of tert-butyl(S)-1-((2S,3S)-1-acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (65 mg, 108 μmol) in CH2Cl2 (434 μl) was added TFA (108 μl). The reaction was stirred for 2.5 h, then concentrated and purified by reverse phase preparative HPLC to provide, after extraction from sat. aq. NaHCO3 and lyophilzation, (S)-N-((2S,3S)-1-acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide (27.2 mg, 50%) as a white solid. MS m/z 500 (MH)+.

후처리

  1. concentrationconcentrated
  2. custompurified by reverse phase preparative HPLC
  3. customto provide
  4. extractionafter extraction from sat. aq. NaHCO3 and lyophilzation, (S)-N-((2S,3S)-1-acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide (27.2 mg, 50%) as a white solid

출처 및 근거

ORD 기록
ord-2fbe1d5a99424d0488a217da52216d72
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422331B2

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