Acetic Acid → HCID 10367597, compound

HRID 860994Notes

Reaction equation

HRID 860994 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[C:20]([C:28]([S:31]([CH3:34])(=[O:33])=[O:32])([CH3:30])[CH3:29])[CH:21]=[C:22]4[C:27]=3[N:26]=[CH:25][CH:24]=[CH:23]4)[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[Li+].[OH-].CC(O)=O>>[CH3:34][S:31]([C:28]([C:20]1[CH:21]=[C:22]2[C:27](=[C:18]([C:14]3[CH:13]=[C:12]([C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])[CH:7]=4)[CH:17]=[CH:16][CH:15]=3)[CH:19]=1)[N:26]=[CH:25][CH:24]=[CH:23]2)([CH3:30])[CH3:29])(=[O:33])=[O:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 69373967HCID 69373967, compound

Product 1

HCID 10367597HCID 10367597, compound

Procedure

To a solution of 3-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl-3-yl}-propionic acid methyl ester (1.0 eq.) from step 1, in TBF:MeOH (2:1; 0.2M) was added aqueous LiOH (2M; 4.0 eq.). The mixture was stirred for 12 h at rt, quenched with AcOH (20 eq.), poured in saturated aqueous NH4OAc and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Crystallization in Hex:CH2Cl2 afforded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrystallization in Hex

Sources & evidence

ORD record
ord-46523050ce4b4120a0c3e21526193c94
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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