Triethylamine → HCID 70980720、化合物

HRID 1749078ノート

反応式

HRID 1749078 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9](Cl)[N:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>CC#N>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:27]=2[O:26][CH3:25])[N:8]=1)[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 13245756Ethyl 2-[(6-chloro-3-nitro-2-pyridinyl)oxy]acetate

生成物 1

HCID 70980720HCID 70980720、化合物収率 79.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a cooled (˜10° C.) solution of (6-chloro-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (8.0 g, 30.8 mmol) in MeCN (80 mL) was added a solution of triethylamine (6.4 mL, 46 mmol) and 2,4-dimethoxybenzylamine (5.5 mL, 37 mmol). The mixture was then stirred for 16 hours at ambient temperature and then concentrated in vacuo. The residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution. The EtOAc layer was then washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using SiO2 chromatography (10-50% EtOAc/Petrol) to give [6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridin-2-yloxy]acetic acid ethyl ester (9.53 g) as a yellow solid. MS: [M+H]+ 392

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution
  3. washThe EtOAc layer was then washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

出典と根拠

ORDレコード
ord-e92a3be54b6d4d42b4c82659aa8857bc
出典データセット
uspto-grants-2015_10
特許番号
US09155743B2

反応ノート

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