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

HRID 716396ノート

反応式

HRID 716396 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8321b48e817542a784b58baa598ae8cf
出典データセット
uspto-grants-2015_11
特許番号
US09187522B2

反応ノート

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