Ethyl Salicylate → Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate

HRID 85391

反応式

HRID 85391 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]([O:17][C:18]([NH:20][CH:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:13]([O:17][C:18]([NH:20][CH:21]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:22]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:23])=[O:19])([CH3:16])([CH3:14])[CH3:15]

参加物

6

反応物 4

HCID 8365Ethyl SalicylateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 2696982-{[(Tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid

生成物 1

HCID 67173975Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate収率 96.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of ethyl 2-hydroxybenzoate (0.5 g, 3.0 mmol) in CH2Cl2 (8 mL) was added 2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (0.8 g, 3.0 mmol), EDCI (0.63 g, 3.3 mmol) and dimethylaminopyridine (0.037 g, 0.3 mmol). The reaction was stirred (RT, 3 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4. The crude material was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to afford ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate (1.2 g). Mass calculated for C235H27NO6=413.46; found: [M+Na]+=437.1.

後処理

  1. custompartitioned between CH2Cl2 and brine
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. customThe crude material was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-95cc40b53c754e7d88aa833f6e43ab20
出典データセット
uspto-grants-2014_09
特許番号
US08846972B2

関連ノート

読み込み中…