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

HRID 1775812Notes

Reaction equation

HRID 1775812 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ee5fb67f9af94e0fa7831b96362ffea6
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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