Trifluoroacetic acid → N-[(1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic Acid

HRID 397459노트

반응식

HRID 397459 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:33])[CH2:31][F:32])[CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][CH:21]([C:30](=[O:33])[CH2:31][F:32])[CH2:22][C:23]([OH:25])=[O:24])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86584009N-[(1-methylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester

생성물 1

HCID 18335070N-[(1-Methylindole-2-Carbonyl)Valinyl]-3-Amino-4-Oxo-5-Fluoropentanoic Acid수율 72.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-[(1-methylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-fluoropentanoic acid, t-butyl ester (19 mg, 0.041 mmol) and anisole (0.1 mL) in CH2Cl2 (1 mL) was treated with trifluoroacetic acid (0.5 mL) at room temperature. After 30 min the reaction mixture was concentrated and chased with methylene chloride. The crude residue was triturated with diethyl ether and the solid filtered to afford the title compound as a light brown solid (12 mg, 72% yield). TLC(AcOH:MeOH:CH2 Cl2, 1:1:20): Rf=0.59. Mass Spectrum for C20H24FN3O5: [MH]+406, [MH]404.

후처리

  1. concentrationAfter 30 min the reaction mixture was concentrated
  2. customThe crude residue was triturated with diethyl ether
  3. filtrationthe solid filtered

출처 및 근거

ORD 기록
ord-2750d94d21a84d069785e6b4e3ec9fe7
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610683B2

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