HCID 69129256, compound → HCID 18508222, compound

HRID 1356217Notes

Reaction equation

HRID 1356217 reaction equation
C([O:5][C:6](=[O:47])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:17](=[O:29])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][C:10]=1[O:39]CC1C=CC=CC=1)(C)(C)C.[H][H]>[OH-].[OH-].[Pd+2]>[C:31]([NH:30][CH:16]([C:17](=[O:29])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:47])=[O:5])=[C:10]([OH:39])[CH:11]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 69129256HCID 69129256, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18508222HCID 18508222, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideSolvent

Procedure

{4-[2-Benzoylamino-2-(4-phenyl-butylcarbamoyl)-vinyl]-2-benzyloxy-phenoxy}-acetic acid tert-butyl ester of Step C (80 mg, 0.13 mmol) is dissolved in ETOH (2 mL) and Pd(OH)2 (13 mg) on carbon is added. Hydrogen is applied and stirred overnight. The mixture is filtered through 0.45 μm Gelman Acrodisc and the filtrate is concentrated to oil. The oil is dissolved in TFA (2 mL). After 3 hours, the TFA is removed by evaporation. The crude material is purified by reverse phase chromatography (C18, CH3CN/H2O) to provide the title compound (compound 40), {4-[2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-hydroxy-phenoxy}-acetic acid; 1H NMR (400 MHz, DMSO-d6): δ8.40 (d, 2H), 7.95 (t, 1H), 7.78 (d, 2H), 7.49 (m, 1H), 7.41 (m, 2H), 7.23 (m, 2H), 7.15 (m, 3H), 6.75 (s, 1H), 6.68 (d, 1H), 6.62 (d, 1H), 4.54 (m, 1H), 4.48 (s, 2H), 3.08 (m, 2H), 2.85 (m, 2H), 2.54 (m, 2H), 1.52 (m, 2H), 1.40 (m, 2H); MS (ES+) m/z 491 (M+1).

Workup

  1. additionis added
  2. filtrationThe mixture is filtered through 0.45 μm Gelman Acrodisc
  3. concentrationthe filtrate is concentrated to oil
  4. dissolutionThe oil is dissolved in TFA (2 mL)
  5. waitAfter 3 hours
  6. customthe TFA is removed by evaporation
  7. customThe crude material is purified by reverse phase chromatography (C18, CH3CN/H2O)

Sources & evidence

ORD record
ord-3e32846d71ea4f1db35c396facc1da5c
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

Loading…