Diisopropylethylamine → HCID 67005474, compound

HRID 563139Notes

Reaction equation

HRID 563139 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1.ClC(N(C)C)=C(C)C.CCN(C(C)C)C(C)C.[CH3:33][O:34][C:35](=[O:57])[C@@H:36]([NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:48][CH:47]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.O>[CH3:33][O:34][C:35](=[O:57])[C@@H:36]([N:44]([CH2:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:48][CH:47]=1)[C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 57486057HCID 57486057, compound

Product 1

HCID 67005474HCID 67005474, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere trans-4-(trifluoromethyl)-cinnamic acid (6.7 g, 31.2 mmol) was dissolved in DCM (150 mL) and 1-chloro-N,N,2-trimethylpropenylamine (4.7 g, 35.5 mmol) was slowly added via syringe. Stirring was continued for 1 h followed by the addition of DIPEA (10.7 mL, 62.6 mmol) and 2-(4-pentyl-benzylamino)-(S)-3-phenyl-propionic acid methyl ester (7.0 g, 20.8 mmol). Stirring was continued for 45 min. Water (250 mL) was added and the product was extracted with DCM (3×150 mL). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silicagel, EtOAc/heptane=¼) to give 6.71 g (59%) of 2-{(4-pentyl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-(S)-3-phenyl-propionic acid methyl ester. LC-MS: tR=1.21 min; [M+H]+=538.38.

Workup

  1. stirringStirring
  2. waitwas continued for 45 min
  3. extractionthe product was extracted with DCM (3×150 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customto give the crude product which
  8. customwas purified by column chromatography (silicagel, EtOAc/heptane=¼)

Sources & evidence

ORD record
ord-b32b6389735446cf9021de5675651afa
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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