Hydrochloric Acid → D-Alanine N-(2-methylthio-2,4-dimethylpentan-3-yl)amide

HRID 648339ノート

反応式

HRID 648339 の反応式
C(OC([NH:8][C@@H:9]([C:11](O)=[O:12])[CH3:10])=O)(C)(C)C.C(N(CC)CC)C.ClC(OCC)=O.[CH3:27][S:28][C:29]([CH3:36])([CH:31]([NH2:35])[CH:32]([CH3:34])[CH3:33])[CH3:30].Cl>C(OCC)(=O)C.C(O)CCC.O.C(O)(=O)C.CO.O1CCCC1>[CH3:27][S:28][C:29]([CH3:36])([CH:31]([NH:35][C:11](=[O:12])[C@@H:9]([CH3:10])[NH2:8])[CH:32]([CH3:34])[CH3:33])[CH3:30]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 637606BOC-D-alanineHCID 144058322-Methylthio-2,4-dimethyl-3-aminopentane

生成物 1

HCID 14405834D-Alanine N-(2-methylthio-2,4-dimethylpentan-3-yl)amide

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 22056973Butanol acetic acid water溶媒

実験手順

To a solution of 3.2 g. (0.017 mole) N-t-butoxycarbonyl-D-alanine and 2.5 g. (0.017 mole) triethylamine in 100 ml. of tetrahydrofuran at -15° C. was added 1.63 ml. of ethyl chloroformate. After stirring for 15 minutes, 2.49 g. (0.017 mole) 2-methylthio-2,4-dimethyl-3-aminopentane was added and the mixture stirred for one hour. The reaction mixture was diluted with ethyl acetate, washed with water, 5% aqueous citric acid (w/v), sodium bicarbonate solution and brine. The organic phase was evaporated to provide 6.0 g. of residue. This was taken up in 100 ml. methanol, 60 ml. of concentrated hydrochloric acid added and the mixture refluxed for one hour. After evaporation of methanol, the residue was taken up in water, washed with ether, the aqueous phase adjusted to pH 12 with sodium hydroxide and extracted wtih ethyl ether. Evaporation of the extracts gave 3.2 g. (87%) of product as a colorless oil Rf 0.56 (butanol/water/acetic acid-4:1:1 by volume).

後処理

  1. stirringthe mixture stirred for one hour
  2. washwashed with water, 5% aqueous citric acid (w/v), sodium bicarbonate solution and brine
  3. customThe organic phase was evaporated
  4. customto provide 6.0 g
  5. temperaturethe mixture refluxed for one hour
  6. customAfter evaporation of methanol
  7. washwashed with ether
  8. extractionextracted wtih ethyl ether
  9. customEvaporation of the extracts
  10. customgave 3.2 g

出典と根拠

ORDレコード
ord-9fd7883e5fae4f9e817ec054c57e69a9
出典データセット
uspto-grants-1983_10
特許番号
US04411925

反応ノート

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