Hydrochloric Acid → 3-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidine

HRID 2038448노트

반응식

HRID 2038448 반응식
[C:1]([O:5]C([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:9]1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.O1CCOCC1>[NH3:8].[CH3:1][OH:5].[CH3:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])=[CH:14][C:13]=1[O:12][CH:10]1[CH2:9][NH:8][CH2:11]1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67342335HCID 67342335, 화합물

생성물 2

HCID 21705897Ammonia methanol수율 10%HCID 461964483-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidine수율 122.9%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To title compound of Step E (0.062 g, 0.146 mmol) in EtOAc (2 mL) was added 4M HCl in dioxane (2 mL). After 18 h, the reaction was neutralized with saturated NaHCO3 (aq.) and extracted with CH2Cl2 (2×). The combined organics were dried and concentrated. Silica gel chromatography (10-80% 2M NH3/MeOH in CH2Cl2) gave 0.029 g (61%) of the title compound. MS (ESI): mass calcd. for C17H16F3NO2, 323.11; m/z found, 324.2 [M+H]+. 1H NMR (CDCl3): 7.73 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.3 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.90 (td, J=8.2, 5.1 Hz, 2H), 6.59 (s, 1H), 5.02-4.97 (m, 1H), 3.92 (s, 3H), 3.96-3.85 (m, 7H).

후처리

  1. extractionextracted with CH2Cl2 (2×)
  2. customThe combined organics were dried
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8221b41625ac484aae9c307704e12e05
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575364B2

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