Ethyl Acetate → Tert-butyl (2-((4-iodobenzyl)amino)-2-oxoethyl)carbamate

HRID 2284792ノート

反応式

HRID 2284792 の反応式
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1.CN1CCOCC1.ClC(OCC(C)C)=O>[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 16217505(4-Iodophenyl)methanamine hydrochloride

生成物 1

HCID 90052505Tert-butyl (2-((4-iodobenzyl)amino)-2-oxoethyl)carbamate収率 118.8%

試薬・触媒・溶媒 3

HCID 79724-Methylmorpholine溶媒HCID 8028Tetrahydrofuran溶媒HCID 62365Isobutyl chloroformate溶媒

実験手順

To a solution of N-Boc-glycine (325 mg) in tetrahydrofuran (3 mL), N-methylmorpholine (1.0 mL) and isobutyl chloroformate (244 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, 4-iodobenzylamine hydrochloride (250 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain tert-butyl (2-((4-iodobenzyl)amino)-2-oxoethyl)carbamate (R4, 430 mg).

後処理

  1. stirringthe mixture was stirred at the same temperature for 1 hour and 30 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-a576e91110cf4bc78969bea3e83c59ae
出典データセット
uspto-grants-2015_09
特許番号
US09145415B2

反応ノート

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