Hydrochloric Acid → O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

HRID 1836604노트

반응식

HRID 1836604 반응식
[C:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][OH:18])[NH:8]C(OC(C)(C)C)=O)([CH3:4])(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:39][C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.[ClH:59]>O1CCCC1.C(O)C>[ClH:59].[CH2:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][O:18][C:43]1[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=1)[NH2:8])[CH3:4]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

생성물 1

HCID 68613683O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of BOC-L-homoserine t-butyl ester (3.2 g, 11.6 mmol) in tetrahydrofuran is added triphenylphosphine (7.59 g, 29 mmol), p-fluorophenol (2.08 g, 18.6 mmol) and 1,1′-azobis(N,N-dimethylformamide) (3.2 g, 18.6 mmol). The mixture is stirred overnight, washed with brine, dried over MgSO4, and the solvent is removed to give an orange oil. The oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate) to give a clear oil which is dissolved in ethanol (100 mL) and the solution is saturated with HCl gas, then stirred overnight. The mixture is concentrated to give O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride as a white solid.

후처리

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customthe solvent is removed
  4. customto give an orange oil
  5. customThe oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate)
  6. customto give a clear oil which
  7. stirringstirred overnight
  8. concentrationThe mixture is concentrated

출처 및 근거

ORD 기록
ord-3451224190f243ac99dca055d6cf1663
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777443B2

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