Gamma-Aminobutyric Acid → HCID 86613534, 화합물

HRID 2237736노트

반응식

HRID 2237736 반응식
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][C@H:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32].[NH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O.[OH-].[Na+].Cl>C(O)(C)C>[OH:12][C@H:11]([C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:9][C@H:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:5]=1)[CH:22]([CH3:23])[CH3:24])[CH2:13][N:33]1[CH2:34][CH2:35][CH2:36][C:37]1=[O:39]

참가 물질

6

반응물 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59849018HCID 59849018, 화합물

생성물 1

HCID 86613534HCID 86613534, 화합물

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
60 °C

실험 절차

A solution of 0.025 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (Example 1b) in 0.50 ml of isopropanol is admixed successively with 0.027 g of 4-aminobutyric acid and 0.13 ml of 1M NaOH and stirred at 60° C. over 3 hours. The reaction mixture is cooled to 0° C. and admixed with 0.13 ml of 1M HCl and concentrated by evaporation to dryness. The residue is dissolved in 2.5 ml of dichloromethane, admixed successively with 0.016 g of N,N-dicyclohexylcarbodiimide and 0.012 mg of 1-hydroxybenzotriazole, and stirred at room temperature over 18 hours. The reaction solution is admixed with 1M sodium hydrogen carbonate solution and extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.32 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.51 (gradient I).

후처리

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. concentrationconcentrated by evaporation to dryness
  3. dissolutionThe residue is dissolved in 2.5 ml of dichloromethane
  4. stirringstirred at room temperature over 18 hours
  5. extractionextracted with ethyl acetate (2×)
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-2ac7bf3b3e474d86a0f1ab468010f9a5
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718675B2

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