Trifluoroacetic acid → N-((7-(3-Pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868757노트

반응식

HRID 1868757 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])[C:13](=[O:19])[C:14]3([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[CH:2]=1.C(O)(C(F)(F)F)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[C:13](=[O:19])[C:14]3([CH3:17])[CH3:18])=[CH:9][CH:8]=2)[CH:2]=1

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 671000221,1-Dimethylethyl N-((7-(3-pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

생성물 1

HCID 57983358N-((7-(3-Pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine수율 59.5%

실험 절차

1,1-Dimethylethyl N-((7-(3-pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (184 mg, 436 μmol) was stirred in TFA (2 mL, 26924 μmol) at room temperature for 30 minutes. The reaction mixture was partitioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give the desired product as a yellow solid (95 mg). MS (m/e)=367.2 (M+H)+. Calculated for C21H19NO5 366.12.

후처리

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-55475314e2304b4ab605eed81e6e6c67
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

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