4-Methylmorpholine → HCID 86650306, compound

HRID 709462Notes

Reaction equation

HRID 709462 reaction equation
[Cl:1][C:2]([Cl:32])([Cl:31])[CH2:3][O:4][C:5](=[O:30])[CH:6]([S:18]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:20])=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[F:62][C:63]([F:73])([F:72])[C:64]1[CH:71]=[CH:70][C:67]([CH2:68]O)=[CH:66][CH:65]=1>CN(C=O)C.CCOC(C)=O>[Cl:32][C:2]([Cl:31])([Cl:1])[CH2:3][O:4][C:5](=[O:30])[CH:6]([S:18]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)(=[O:20])=[O:19])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH2:68][C:67]2[CH:66]=[CH:65][C:64]([C:63]([F:62])([F:72])[F:73])=[CH:71][CH:70]=2)=[O:16])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 676844-(Trifluoromethyl)benzenemethanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66866218HCID 66866218, compound

Product 1

HCID 86650306HCID 86650306, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Carboxymethyl-phenyl)-2-[2-(4-fluoro-phenyl)-ethanesulfonyl]-propionic acid 2,2,2-trichloro-ethyl ester (121 mg, 0.23 mmol) was dissolved in anhydrous DMF (2.0 mL) and TBTU (147 mg, 0.46 mmol), N-methyl morpholine (46.5 mg, 0.46 mmol) and 4-(trifluoromethyl)benzyl alcohol (81.06 mg, 0.46 mmol) were added under nitrogen atmosphere. The reaction was stirred at ambient temperature for 18 h. EtOAc was added and the mixture was extracted with water and brine. After drying the organic layer over Na2SO4 the solvent was evaporated under reduced pressure to afford the crude product as an oil (161 mg, 102.3%). No further purification was done. 1H NMR (400 MHz, CDCl3): δ 7.44-7.62 (m, 6H), 7.12-7.23 (m, 4H), 6.97-7.02 (t, 2H) 5.14 (s, 2H), 4.74 (s, 2H), 4.69 (d, 1H), 3.62 (s, 2H), 3.34-58 (m, 4H), 3.15-3.19 (t, 2H).

Workup

  1. extractionthe mixture was extracted with water and brine
  2. dry with materialAfter drying the organic layer over Na2SO4 the solvent
  3. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-6a2d18f9fdef4bd591cb9cd06f93e5c8
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

Loading…