2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → HCID 67529665, compound

HRID 219961Notes

Reaction equation

HRID 219961 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[NH2:20][C:21](=[N:35]O)[C:22]1[C:31]([O:32][CH3:33])=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([Cl:34])[CH:23]=1>>[Cl:34][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:12][N:35]=2)[C:31]([O:32][CH3:33])=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

3

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307483HCID 72307483, compound

Product 1

HCID 67529665HCID 67529665, compound

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 28 (99.09 mg; 0.39 mmol) and Intermediate 59 (100 mg; 0.39 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1). The white solid was washed with MeOH affording the title compound as an off-white powder. LC/MS (Method B): 479.2 (M+H)+. HPLC (Method A) Rt 5.86 min (Purity: 98.1%).

Workup

  1. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  2. washrinsed with ACN
  3. washrinsed with ACN
  4. customAfter evaporation of the solvents
  5. customthe crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)
  6. washThe white solid was washed with MeOH affording the title compound as an off-white powder

Sources & evidence

ORD record
ord-abd96685196f4873964f7b6418ab45fa
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

Loading…