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

HRID 716396노트

반응식

HRID 716396 반응식
C([NH2:4])(=O)C.[C:5]([C:9]1[CH:49]=[CH:48][C:12]([C:13]([NH:15][C@H:16]([C:44]([O:46][CH3:47])=[O:45])[CH2:17][C:18]2[CH:43]=[CH:42][C:21]([C:22]([O:24][CH2:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=3)=O)=O)=[CH:20][CH:19]=2)=[O:14])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CC(=O)OCC>[C:5]([C:9]1[CH:49]=[CH:48][C:12]([C:13]([NH:15][C@@H:16]([CH2:17][C:18]2[CH:43]=[CH:42][C:21]([C:22]3[O:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=4)[N:4]=3)=[CH:20][CH:19]=2)[C:44]([O:46][CH3:47])=[O:45])=[O:14])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

참가 물질

4

반응물 2

HCID 178AcetamideHCID 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 borontrifluoride 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 RT, 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 recrystallised 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 RT
  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 recrystallised from Et2O (5 mL)
  7. filtrationfiltered
  8. washrinsed with Et2O
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-8321b48e817542a784b58baa598ae8cf
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187522B2

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