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Sodium Carbonate → (1S,6R)-tert-Butyl 8-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

HRID 2174999
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HRID 2174999 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)[C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[C@H:20]12[NH:27][CH2:26][C@H:25]1[CH2:24][CH2:23][N:22]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:21]2.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)[C:3]=1[C:4]([N:27]1[C@H:20]2[C@H:25]([CH2:24][CH2:23][N:22]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:21]2)[CH2:26]1)=[O:6]
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7

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HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 16099093(1S,6R)-3-Boc-3,8-diazabicyclo[4.2.0]octaneHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

생성물 1

HCID 67086932(1S,6R)-tert-Butyl 8-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

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온도
50 °C

실험 절차

To 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (406 mg, 1.5 mmol) in PhCH3 (5 mL) was added SOCl2 (117 μL, 1.6 mmol). The flask was heated with an oil bath to 50° C. for 1 h. To (1S,6R)-tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate (260 mg, 1.3 mmol) and Na2CO3 (519 mg, 4.9 mmol) in PhCH3 (5 mL) and H2O (5 mL) at 0° C. was added the above solution dropwise. The reaction was allowed to warm slowly to rt and stir for 15 h and extracted with DCM (2×). The combined organics were dried (Na2SO4). Purification via silica gel chromatography (1-7% 2M NH3/MeOH in CH2Cl2) gave 335 mg (68%) of the title compound. MS (ESI) mass calcd. C20H24FN5O3, 401.44; m/z found 346.1 [M−C(CH3)3]+.

후처리

  1. temperatureto warm slowly to rt
  2. extractionextracted with DCM (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customPurification via silica gel chromatography (1-7% 2M NH3/MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-6b0d12ccdd934e1a8c3c40308791f92e
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062044B2

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