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4-Methylmorpholine → 1,1-Dimethylethyl N-[1,1-dimethyl-2-(methylamino)-2-oxoethyl]carbamate

HRID 1867767
ノート
印刷プレビュー

反応式

HRID 1867767 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11](O)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][N:16]1CCOCC1.C(OC(Cl)=O)C(C)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([NH:16][CH3:15])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[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

5

反応物 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

生成物 1

HCID 474517541,1-Dimethylethyl N-[1,1-dimethyl-2-(methylamino)-2-oxoethyl]carbamate収率 42.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-(tert-butoxycarbonyl)-2-methylalanine (2.87 g, 14.13 mmol) was dissolved in THF (20 ml) and cooled to −10° C. (acetone/ice). N-methylmorpholine (2.14 g, 21.2 mmol) was added followed by iso-butylchloroformate (2.12 g, 15.5 mmol, 1.1 equivalents) over a period of 3 minutes. The reaction mixture was allowed to stir for 10 minutes, split in two equal halves (approximately 12 ml each). One sample was treated with methylamine in THF (5 ml of 2.0M solution) and the resulting mixture was evaporated to dryness. The residues were re-dissolved in dichloromethane (30 ml), washed with water, saturated aqueous sodium hydrogen carbonate, water, dried over magnesium sulfate and evaporated to dryness to give N2-(tert-butoxycarbonyl)-N1,2-dimethylalaninamide (0.67 g, 42.6%), which was used without further purification, 1H NMR Spectrum: (DMSO-d6) 1.29 (s, 6H), 1.37 (s, 9H), 2.50 (s, 3H), 6.57 (br s, 1H), 6.93 (br s, 1H)

後処理

  1. customsplit in two equal halves (approximately 12 ml each)
  2. additionOne sample was treated with methylamine in THF (5 ml of 2.0M solution)
  3. customthe resulting mixture was evaporated to dryness
  4. dissolutionThe residues were re-dissolved in dichloromethane (30 ml)
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate, water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-9e6a431dfa874bad9b13db3e75d6a929
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632840B2

反応ノート

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