Benzyl Bromide → Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

HRID 1785844ノート

反応式

HRID 1785844 の反応式
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.[Ag]=O>[CH2:16]([O:4][CH2:3][C@@H:2]([C:5]([O:7][CH3:8])=[O:6])[NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 495564Methyl N-(tert-butoxycarbonyl)serinate

生成物 1

HCID 14427182Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of BOC-DL-Ser-OMe (434 mg, 2.0 mmol), benzyl bromide (513 mg, 3.0 mmol), and silver oxide (695 mg, 3.0 mmol) in dichloromethane (10 mL) at room temperature was stirred for 2 days, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 308 (M−H)−.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-333c17c03f8044eb9956ea3aae74859d
出典データセット
uspto-grants-2009_03
特許番号
US07504512B2

反応ノート

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