Triethylamine → HCID 57962249、化合物

HRID 541831ノート

反応式

HRID 541831 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37](O)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.O1CCCC1>[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 24386Thionyl ChlorideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

生成物 1

HCID 57962249HCID 57962249、化合物収率 95.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

tert-Butyl (3-aminophenyl)carbamate (1.0 g, 4.8 mmol) was dissolved in methylene chloride (4 mL) and then thionyl chloride (2.0 mL, 27 mmol) was added. The mixture was heated at 80° C. for 1 h. The solvent was removed under vacuum. Tetrahydrofuran (20 mL), triethylamine (2.3 mL, 17 mmol) and (3-nitrophenyl)acetic acid (0.87 g, 4.8 mmol) were then added and the mixture was stirred at rt for 1 h. The solvent was removed under vacuum and then EtOAc and water were added. The aqueous phase was extracted again with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a white powder (1.70 g, 95%). LCMS for C19H21N3O5 (M-tBu+H)+: m/z=316.0.

後処理

  1. customThe solvent was removed under vacuum
  2. customThe solvent was removed under vacuum
  3. additionEtOAc and water were added
  4. extractionThe aqueous phase was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e2541d32f1104380a9192b61b1a40acb
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

反応ノート

読み込み中…