Acetamide → (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(4-(4-(heptyloxy)phenyl)oxazol-2-yl)phenyl)propanoate

HRID 1775812노트

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HRID 1775812 반응식
B(F)(F)F.CCOCC.C([NH2:13])(=O)C.[C:14]([C:18]1[CH:58]=[CH:57][C:21]([C:22]([NH:24][C@H:25]([C:53]([O:55][CH3:56])=[O:54])[CH2:26][C:27]2[CH:52]=[CH:51][C:30]([C:31]([O:33][CH2:34][C:35]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:39][CH:38]=3)=O)=O)=[CH:29][CH:28]=2)=[O:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>CC(=O)OCC>[C:14]([C:18]1[CH:58]=[CH:57][C:21]([C:22]([NH:24][C@@H:25]([CH2:26][C:27]2[CH:52]=[CH:51][C:30]([C:31]3[O:33][CH:34]=[C:35]([C:37]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:39][CH:38]=4)[N:13]=3)=[CH:29][CH:28]=2)[C:53]([O:55][CH3:56])=[O:54])=[O:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 86689660(S)-2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoate

생성물 1

HCID 86689661(S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(4-(4-(heptyloxy)phenyl)oxazol-2-yl)phenyl)propanoate수율 35.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

To boron trifluoride diethyl etherate (33.3 μl, 0.27 mmol) was added a mixture of acetamide (763 mg, 12.9 mmol) and (S)-2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-(2-(4-(tert-butyl)benzamido)-3-methoxy-3-oxopropyl)benzoate (159 mg, 0.26 mmol). The reaction mixture was stirred at 140° C. for 1 h. The reaction mixture was allowed to cool to room temperature, diluted with EA (15 mL) and extracted with NaHCO3 (3×15 mL) and brine (15 mL). The combined organics were dried over MgSO4, filtered and concentrated. The residue was recrystallized from Et2O (5 mL), filtered and rinsed with Et2O. The filtrate was concentrated to afford 55 mg (16%) of (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-(4-(4-(heptyloxy)phenyl)oxazol-2-yl)phenyl)propanoate as an orange oil. LCMS-ESI (m/z) calculated for C37H44N2O5: 596.8. found 597.0 [M+H]+, tR=3.11 min. (Method 4).

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with NaHCO3 (3×15 mL) and brine (15 mL)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from Et2O (5 mL)
  7. filtrationfiltered
  8. washrinsed with Et2O
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-ee5fb67f9af94e0fa7831b96362ffea6
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260427B2

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