Citric Acid → (R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

HRID 454971

반응식

HRID 454971 반응식
C[O:2][C:3](=O)[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.B.[Li].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:16]([O:15][C:13](=[O:14])[NH:12][C@H:4]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH2:3][OH:2])([CH3:19])([CH3:17])[CH3:18]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 10934864Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetateHCID 178419226HCID 178419226, 화합물

생성물 1

HCID 67073553(R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(R)-tert-Butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid methyl ester (10 mmol), Lithium Boron hydride (1.089 g, 50 mmol) and THF (50 ml) were combined and stirred at room temperature overnight. Ice (20 ml) was added into the reaction mixture with stirring. Saturated citric acid was then added dropwise until no more bubbles were generated. The reaction mixture was transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with saturated NH4Cl and water sequentially, then dried over MgSO4, filtered and concentrated to give a white crude solid (2.92 g, crude product) with some impurity: 1H NMR (400 MHz, MeOD) δ ppm 7.14 (d, J=8.6 Hz, 2H), 6.76 (d, J=8.6 Hz, 2H), 4.56 (m, 1H), 3.63 (m, 2H), 1.43 (s, 9H); LCMS (ESI) m/e 254.1 [(M+H)+, calcd for C13H20NO4 254.3].

후처리

  1. stirringwith stirring
  2. customThe reaction mixture was transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×30 ml)
  4. washThe combined organic layers were washed with saturated NH4Cl and water sequentially
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white crude solid (2.92 g, crude product) with some impurity

출처 및 근거

ORD 기록
ord-ce7005a1ecff4913a3d6285bed6bfa2d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497271B2

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