Acetic Acid → HCID 10005693, compound

HRID 861023Notes

Reaction equation

HRID 861023 reaction equation
COC(=O)[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[C:22]([C:30]([S:33]([CH3:36])(=[O:35])=[O:34])([CH3:32])[CH3:31])[CH:23]=[C:24]4[C:29]=3[N:28]=[CH:27][CH:26]=[CH:25]4)[CH:15]=2)=[CH:10][CH:9]=1)(C)[CH3:6].[Li+].[OH-].C[C:41]([OH:43])=[O:42]>C1COCC1.CO.[Cl-].[Na+].O>[CH3:36][S:33]([C:30]([C:22]1[CH:23]=[C:24]2[C:29](=[C:20]([C:16]3[CH:15]=[C:14]([C:11]4[CH:10]=[CH:9][C:8]([C:5]([CH3:6])([CH3:4])[C:41]([OH:43])=[O:42])=[CH:13][CH:12]=4)[CH:19]=[CH:18][CH:17]=3)[CH:21]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)([CH3:32])[CH3:31])(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 69373991HCID 69373991, compound

Product 1

HCID 10005693HCID 10005693, compound

Reagents, catalysts & solvents 2

HCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-4-yl}-3-methyl-butyric acid methyl ester (1.0 eq.) from Step 1, in THF:MeOH (2:1; 0.2M) was added aqueous LiOH (2M; 5.0 eq.). The mixture was stirred for 4 h at 60° C., quenched with AcOH (20 eq.), poured in brine and extracted with EtOAc (2×). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Crystallization in Hex:Et2O:EtOAc afforded the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 8.93 (dd, 1H), 8.46 (dd, 1H), 8.29 (d, 1H), 8.21 (d, 1H), 8.02 (t, 1H), 7.72–7.68 (m, 4H), 7.59–7.51 (m, 4H), 2.72 (s, 3H), 2.00 (s, 6H), 1.59 (s, 6H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrystallization in Hex

Sources & evidence

ORD record
ord-ca5c02feef2345d3813856108424f93c
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

Loading…