Salicylic Acid → Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate

HRID 919148

反応式

HRID 919148 の反応式
[NH2:1][CH:2]([CH3:16])[CH:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[OH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[OH:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][CH:2]([CH3:16])[CH:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4])=[O:21]

参加物

6

反応物 4

HCID 338Salicylic AcidHCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 59193262Benzyl 3-aminobutan-2-ylcarbamate

生成物 1

HCID 67174902Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate収率 40%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a mixture of benzyl 3-aminobutan-2-ylcarbamate (5.3 g, 23.8 mmol), 2-hydroxybenzoic acid (3.28 g, 23.8 mmol) and imidazole (1.62 g, 23.8 mmol) in EtOAc (180 mL) at 0° C. was slowly added a solution of DCC (4.90 g, 23.8 mmol) in EtOAc (20 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with PE-EA (5:1) to afford benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate (3.2 g, 40%) as a colorless oil. Mass calculated for C19H22N2O4=342.39. found: [M+H]+=343.2.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel
  4. washeluting with PE-EA (5:1)

出典と根拠

ORDレコード
ord-623a921d06204cc0b7c8b99cd313927a
出典データセット
uspto-grants-2016_03
特許番号
US09272984B2

関連ノート

読み込み中…