Triethylamine → Ethyl 4-(4-benzylbenzamido)-3-fluorobenzoate

HRID 658976ノート

反応式

HRID 658976 の反応式
[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:30][C:31]1[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][C:32]=1[F:42]>ClCCl.CN(C=O)C>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:30][C:31]2[CH:41]=[CH:40][C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][C:32]=2[F:42])=[O:14])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1364294-Benzylbenzoic acidHCID 20536493Ethyl 4-Amino-3-fluorobenzoate

生成物 1

HCID 57625194Ethyl 4-(4-benzylbenzamido)-3-fluorobenzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 4-benzylbenzoic acid (1.06 g, 5 mmole) in dichloromethane (10 mL) was added oxalyl dichloride (1 mL) followed by a few drops of DMF at 0° C. The resulting mixture was stirred room temperature for 3 hours. Removal of the solvents gave the residue which was dissolved in dichloromethane (2 mL) and added to the solution of triethylamine (1.4 mL, 10 mmol) and ethyl 4-amino-3-fluorobenzoate (916 mg, 5 mmole) in dichloromethane (50 mL) at 0° C. After stirring at room temperature for 48 hours, the mixture was washed with saturated sodium bicarbonate and 1 N HCl. The combined organic extracts were washed with brine, dried and concentrated under reduced pressure to give the residue which was purification by silica gel chromatography on ISCO system. The desired product was obtained as an off white solid: 1H NMR (400 MHz, CDCl3) δ 8.63 (t, J=8.8 Hz, 1H), 8.20 (s, 1H), 7.83 (m, 4H), 7.18-7.35 (m, 6H), 4.39 (q, J=7.2 Hz, 1H), 4.07 (s, 2H), 1.40 (t, J=7.2 Hz, 3H).

後処理

  1. customRemoval of the solvents
  2. customgave the residue which
  3. stirringAfter stirring at room temperature for 48 hours
  4. washthe mixture was washed with saturated sodium bicarbonate and 1 N HCl
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give the residue which
  9. custompurification by silica gel chromatography on ISCO system

出典と根拠

ORDレコード
ord-34960b9d0fe3479db2e3eec0dfe574f4
出典データセット
uspto-grants-2011_12
特許番号
US08080542B2

反応ノート

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