Hydrochloric Acid → (R)-6-cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide

HRID 129940노트

반응식

HRID 129940 반응식
[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[C:25]([CH2:27][C@@H:28]([OH:35])[CH2:29][C:30](OCC)=[O:31])#[N:26].Cl>O1CCCC1.O1CCCC1.CCCCCCC>[C:25]([CH2:27][C@@H:28]([OH:35])[CH2:29][C:30](=[O:31])[CH2:9][C:8]([N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10])#[N:26]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10615N,N-DiphenylacetamideHCID 2724682Lithium diisopropylamideHCID 2733879Ethyl (3R)-4-cyano-3-hydroxybutanoate

생성물 1

HCID 9818592(R)-6-cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21263495Tetrahydrofuran heptane용매

실험 절차

To a stirred -10° C. solution of N,N-diphenylacetamide (211 g, 1.0 mol) in tetrahydrofuran (1.0 L) is slowly added a solution of lithium diisopropylamide in tetrahydrofuran-heptane (0.5 L of 2M) while maintaining the temperature between -10° C. to -5° C. The mixture is stirred at -0° C. to 20° C. for 30 minutes. (R)-4-cyano-3-hydroxybutyric acid, ethyl ester (Brower, supra) (40 9, 0.25 mol) as a solution in 200 mL of tetrahydrofuran is added to the previously prepared anion. The reaction mixture is stirred for 30 minutes at -5° C. to -20° C., and transferred to a 2.2N aqueous hydrochloric acid solution (1 L). The aqueous layer is extracted with 500 mL of ethyl acetate, the aqueous layer is separated and reextracted with 100 mL of ethyl acetate, the extracts are combined and concentrated in vacuo to afford crude (R)-6-cyano-5 -hydroxy-3-oxo-N,N-diphenylhexanamide which is not isolated. A small sample is purified by column chromatography on flash silica gel (60:40 hexane:ethyl acetate) as an oil. Proton nuclear magnetic resonance spectroscopy (1H-NMR): (Acetone-d6) δ 2.02 (m, 2H), 2.73 (m, 2H), 4.1 (m, 2H), 4.52 (m, 1H), 4.74 (s, 1H), 7.2-7.4 (m, 10H).

후처리

  1. temperaturewhile maintaining the temperature between -10° C. to -5° C
  2. stirringThe reaction mixture is stirred for 30 minutes at -5° C. to -20° C.
  3. extractionThe aqueous layer is extracted with 500 mL of ethyl acetate
  4. customthe aqueous layer is separated
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-424fc5ce5e6e496192a6cf3a9deb87e9
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470981

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