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 1486062ノート

反応式

HRID 1486062 の反応式
[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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-2fbe1d5a99424d0488a217da52216d72
出典データセット
uspto-grants-2016_08
特許番号
US09422331B2

反応ノート

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