Diisopropylethylamine → Merimepodib

HRID 503971Notes

Reaction equation

HRID 503971 reaction equation
C1(O[C:8](=[O:26])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17][C:18]([O:20][C@H:21]3[CH2:25][CH2:24][O:23][CH2:22]3)=[O:19])[CH:11]=2)C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH2:40])[CH:32]=[CH:33][C:34]=1[C:35]1[O:39][CH:38]=[N:37][CH:36]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH:40][C:8](=[O:26])[NH:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH2:16][NH:17][C:18](=[O:19])[O:20][C@H:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[CH:32]=[CH:33][C:34]=1[C:35]1[O:39][CH:38]=[N:37][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 154627323-Methoxy-4-(oxazol-5-yl)anilineHCID 17748134(S)-Tetrahydrofuran-3-yl (3-((phenoxycarbonyl)amino)benzyl)carbamate

Product 1

HCID 153241MerimepodibYield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Added 2e (15 g, 1.0 eq) and 2g (8.58 g, 1.07 eq) into a jacketed reactor of suitable size before adding ethyl acetate (225 ml, 15 vol) and diisopropylethylamine (5.43 g, 1.0 eq), then heated the mixture to reflux (75-85° C.) for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature and stirred for an additional 1 hour. Precipitated solid was filtered, washed with EtOAc 2 times (45 ml, 3 vol each wash), then dried at 58° C. for 18 hours (until a LOD is achieved of less than 1%) to give 17.46 g of crude 2h (90.4% yield, 98.46% a/a) as a white crystalline solid.

Workup

  1. temperatureheated the mixture
  2. temperaturethe mixture was cooled to room temperature
  3. customPrecipitated solid
  4. filtrationwas filtered
  5. washwashed with EtOAc 2 times (45 ml, 3 vol
  6. washeach wash),
  7. customthen dried at 58° C. for 18 hours (until a LOD

Sources & evidence

ORD record
ord-abbd557638674de2b1fceebcb1f250da
Source dataset
uspto-grants-2010_08
Patent number
US07777048B2

Reaction notes

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