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

HRID 1027662

反応式

HRID 1027662 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-24c798c8a99f464b958626c2627a6e53
出典データセット
uspto-grants-2014_05
特許番号
US08735379B2

関連ノート

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