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Methyl iodide → Methyl 2-[3-[(tert-Butoxycarbonyl)(methyl)amino]-2,2-dimethylpropoxy]-4-tert-butylbenzoate

HRID 644287
ノート
印刷プレビュー

反応式

HRID 644287 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:28])([CH3:27])[CH2:11][O:12][C:13]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[CH3:31][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.ClCCl>[C:1]([O:5][C:6]([N:8]([CH3:31])[CH2:9][C:10]([CH3:28])([CH3:27])[CH2:11][O:12][C:13]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68530988Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate

生成物 1

HCID 68533360Methyl 2-[3-[(tert-Butoxycarbonyl)(methyl)amino]-2,2-dimethylpropoxy]-4-tert-butylbenzoate収率 61.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate (2.50 g, 6.35 mmol) in THF at 0° C. under N2 was added methyl iodide (4.51 g, 31.8 mmol, 5 eq), followed by sodium bis(trimethylsilyl)amide (12.7 mL, 12.7 mmol, 1.0 M in THF). The cooling bath was allowed to slowly warm to room temperature. The reaction was stirred at room temerature for 2.5 days, then diluted with dichloromethane, washed with water and brine, dried, and concentrated in vacuo to give 1.60 g (61.8%) of the desired product as a viscous oil which was used without further purification.

後処理

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c9caf840ea0e49a6b017fa59e264757d
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700628B2

反応ノート

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