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4-Methylmorpholine → tert-butyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)butyl]carbamate

HRID 269611
ノート
印刷プレビュー

反応式

HRID 269611 の反応式
CN1CCOCC1.ClC(OCC)=O.[C:14]([O:18][C:19]([NH:21][C@H:22]([C:34](O)=[O:35])[CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:20])([CH3:17])([CH3:16])[CH3:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([CH2:34][OH:35])[CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([CH3:15])([CH3:17])[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 7015803Boc-orn(boc)-OHHCID 21226445Aluminium lithium hydride

生成物 1

HCID 86601679tert-butyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)butyl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

91 mg (0.90 mmol) of 4-methylmorpholine and 98 mg (0.90 mmol) of ethyl chloroformate are added to a solution of 300 mg (0.90 mmol) of N2,N5-bis(tert-butoxycarbonyl)-L-ornithine in 10 ml of tetrahydrofuran at −10° C., and the mixture is stirred for 30 min. At this temperature, 1.81 ml (1.81 mmol) of a 1M solution of lithium aluminum hydride in tetrahydrofuran are slowly added dropwise. The mixture is slowly warmed to RT and stirred at RT for 12 h. While cooling in ice, 0.1 ml of water and 0.15 ml of a 4.5% sodium hydroxide solution are cautiously added, and the mixture is stirred at RT for a further 3 h. The mixture is filtered and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and again evaporated to dryness in vacuo. The product is reacted without further purification.

後処理

  1. stirringstirred at RT for 12 h
  2. temperatureWhile cooling in ice
  3. stirringthe mixture is stirred at RT for a further 3 h
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customagain evaporated to dryness in vacuo
  10. customThe product is reacted without further purification

出典と根拠

ORDレコード
ord-7ee5e82a57ec4d5789d59ec3b9ca9c45
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07446102B2

反応ノート

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