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

HRID 2364128ノート

反応式

HRID 2364128 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-785a6cdc8e254678bb9582369aa64494
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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