1-Butanol → Boc-N-Me-Phe-OH

HRID 443921

反応式

HRID 443921 の反応式
[NH:1]([CH3:13])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)CCC.[OH-].[Na+].C(O[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(C)(C)C>O>[CH3:31][C:28]([O:27][C:26]([N:1]([C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:13])=[O:32])([CH3:29])[CH3:30]

参加物

6

反応物 4

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 6951135N-MethylphenylalanineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

生成物 1

HCID 7010602Boc-N-Me-Phe-OH

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

3.6 g of H-MePhe-OH are dissolved in a mixture of ter.-butanol, 25 ml of 10% aqueous KHCO3 solution and 5 ml of 4 N sodium hydroxide. 8 ml of di-tert.-butylcarbonate are added and the mixture stirred for 2 days at room temperature. The reaction mixture is diluted with ca. 100 ml of water and extracted with ether. The aqueous phase is acidified, with stirring to pH 2. The precipitated product is extracted with acetic acid, the extract washed with water and dried over Na2SO4. The liquid is evaporated and the product crystallised from ether/petroleum ether to yield Boc-MePHe-OH. M.P. 87°.

後処理

  1. extractionextracted with ether
  2. stirringwith stirring to pH 2
  3. extractionThe precipitated product is extracted with acetic acid
  4. washthe extract washed with water
  5. dry with materialdried over Na2SO4
  6. customThe liquid is evaporated
  7. customthe product crystallised from ether/petroleum ether

出典と根拠

ORDレコード
ord-96ee78c924034d5a92685256586e1f57
出典データセット
uspto-grants-1981_04
特許番号
US04261888

関連ノート

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