Trifluoroacetic acid → Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

HRID 2364128노트

반응식

HRID 2364128 반응식
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([NH:16]C(OC(C)(C)C)=O)[C:10]([C:13]([O-:15])=[O:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.F[C:27](F)(F)[C:28](O)=O>C(Cl)Cl>[NH2:16][C:9]1[C:10]([C:13]([O:15][CH2:27][CH3:28])=[O:14])=[N:11][CH:12]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=2)[CH:8]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 866228435-(4-Fluorobenzyl)-3-[(tert-butoxy)carbonyl]amino-2-pyridinecarboxylate

생성물 1

HCID 42637772Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-(4-fluorobenzyl)-3-[(tert-butoxy)carbonyl]amino-2-pyridinecarboxylate (29 g, 77 mmol) in CH2Cl2 (200 mL) and trifluoroacetic acid (60 mL) was stirred at rt overnight. The solvent was removed in vacuo and the crude material was dissolved in EtOAc and washed with NaHCO3 solution and brine. The organic layer was dried, concentrated and chromatographed on silica gel eluting with 20-60% EtOAc/hexanes to yield the product as a light yellow solid: 1H NMR (d6-DMSO) δ 7.76 (1H, d, J=1.7 Hz), 7.25 (2H, m), 7.15 (2H, t, J=9 Hz), 6.92 (1H, d,J=1.7 Hz), 6.62 (2H, br s), 4.23 (2H, q, J=7 Hz), 3.87 (2H, s), 1.26 (3H, t, J=7 Hz), AP+ MS: 275 (M+H+, 100); HRMS calcd for C15H15FN2O2+H+: 275.1196. Found: 275.1206.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude material was dissolved in EtOAc
  3. washwashed with NaHCO3 solution and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with 20-60% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-785a6cdc8e254678bb9582369aa64494
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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