1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(2-hydroxybutanoyl)glycine benzyl ester

HRID 1092922노트

반응식

HRID 1092922 반응식
[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([O-])=[O:4].[Li+].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([O:27][C:28](=[O:31])[CH2:29][NH2:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[CH2:20]([O:27][C:28](=[O:31])[CH2:29][NH:30][C:3](=[O:4])[CH:2]([OH:1])[CH2:6][CH3:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 23707041Lithium 2-hydroxybutanoate

생성물 1

HCID 66589261N-(2-hydroxybutanoyl)glycine benzyl ester수율 49%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1.50 g (13.6 mmol) of lithium 2-hydroxybutanoate, 4.60 g (13.6 mmol) of glycine benzyl ester p-toluenesulfonic acid salt, and 1.84 g (1.36 mmol) of 1-hydroxybenzotriazole monohydrate (HOBt) were added to 80 mL of acetonitrile and stirred at room temperature for 20 minutes. The mixture was further mixed with 2.61 g (13.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and stirred at room temperature overnight. After the reaction mixture was filtered, the filtrate was vacuum-concentrated and the residue was dissolved in 200 mL of ethyl acetate. Washing with 1N hydrochloric acid and an aqueous solution saturated sodium hydrogen carbonate was carried out successively and drying over anhydrous sodium sulfate was carried out. After the solvent as removed by distillation, the residue was purified by flash column chromatography on silica gel (No. 9385, Merck) using a solvent mixture of hexane and ethyl acetate at 1:2 ratio to obtain N-(2-hydroxybutanoyl)glycine benzyl ester as a colorless oily substance (1.67 g, yield 49%).

후처리

  1. stirringstirred at room temperature overnight
  2. filtrationAfter the reaction mixture was filtered
  3. concentrationthe filtrate was vacuum-concentrated
  4. dissolutionthe residue was dissolved in 200 mL of ethyl acetate
  5. washWashing with 1N hydrochloric acid
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customAfter the solvent as removed by distillation
  8. customthe residue was purified by flash column chromatography on silica gel (No
  9. additiona solvent mixture of hexane and ethyl acetate at 1:2 ratio

출처 및 근거

ORD 기록
ord-524e7b564c4d44d38389264200a88cd8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129557B2

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