Water → HCID 178426557, compound

HRID 1514986Notes

Reaction equation

HRID 1514986 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]=O)=[C:11]([CH3:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][C:37]=1[NH2:38])[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=1)=[O:25].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[NH:38][C:37]3[CH:36]=[CH:35][C:23]([C:24](=[O:25])[NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=4)=[CH:22][C:21]=3[N:20]=2)=[C:11]([CH3:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 2733225Ytterbium triflateHCID 66965643HCID 66965643, compoundHCID 86638180HCID 86638180, compound

Product 1

HCID 178426557HCID 178426557, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-formyl-3,5-dimethylphenyl)-propionic acid tert-butyl ester (200 mg) and 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (Example 5-1, step 6) (194 mg) in DMSO (10 mL) was added Yb(OTf)3 (93 mg). The solution was stirred at room temperature for 18 h then the mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography (amino-column) using hexanes/ethyl acetate (1:4) and gave 3-{4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid tert-butyl ester as a red solid. MS (ESI)m/z 498 (M+H). 1H NMR (Acetone-d6, 400 MHz) δ 11.73 (s, 1H), 9.39 (s, 1H), 8.30 (s, 1H), 7.94 (t, 1H), 7.69 (m, 3H), 7.12 (s, 1H), 7.07 (s, 2H), 2.90 (t, 2H), 2.58 (t, 2H), 2.28 (s, 3H), 2.25 (s, 3H), 2.16 (s, 6H), 1.45 (s, 9H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (amino-column)

Sources & evidence

ORD record
ord-549abd544dc04f85ac838fbc5682d6b9
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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