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

HRID 648339노트

반응식

HRID 648339 반응식
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]

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 22056973Butanol acetic acid water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9fd7883e5fae4f9e817ec054c57e69a9
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04411925

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