Hydroxyphenylacetic acid → HCID 68535772, compound

HRID 1993503Notes

Reaction equation

HRID 1993503 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH3:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[CH:16][CH:15]=1)[CH3:13]

Participants

7

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 79724-MethylmorpholineHCID 115044-EthylanilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68535772HCID 68535772, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxyphenyl acetic acid (1.55 g, 10.2 mmol), 4-ethyl-phenylamine (1.28 ml, 10.3 mmol), TBTU (4.82 g, 15 mmol), and NMM (8.79 ml, 80 mmol) are stirred in DMF (30 ml) at rt for 5 h. The reaction mixture is taken up in AcOEt (0.2 L), washed with H2O (40 ml, 2×) and brine (40 ml, 2×), dried (Na2SO4), concentrated under reduced pressure, and flash chromatographed (silica gel, 3.5×25 cm, AcOEt/hexane=1:2→2:3) giving the title compound of Stage 16.1 as a colorless solid (1.68 g, 6.59 mmol; 66%) M+H=256.1; 1H-NMR (400 MHz, DMSO-d6): 10.0/9.24 (s/s, 1H, NH/OH), 7.46 (d, 8.5 Hz, 2H, phenyl), 7.09 (d, 8.5 Hz, 4H, phenyl), 6.66 (d, 8.5 Hz, 2H, phenyl), 3.47 (s, 2H, aryl-CH2), 2.53 (qu, 7.5 Hz, 2H, CH2), 1.13 (t, 7.5 Hz, 3H, CH3); R. (AcOEt/hexane=1:1): 0.66; m.p. =146-148° C.

Workup

  1. washwashed with H2O (40 ml, 2×) and brine (40 ml, 2×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure, and flash
  4. customchromatographed (silica gel, 3.5×25 cm, AcOEt/hexane=1:2→2:3)

Sources & evidence

ORD record
ord-92004fea7e764eb589e4a9a804442e3f
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…