Lithium Hydroxide → HCID 10345293, compound

HRID 861021Notes

Reaction equation

HRID 861021 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:22]=[C:23]([C:31]([S:34]([CH3:37])(=[O:36])=[O:35])([CH3:33])[CH3:32])[CH:24]=[C:25]4[C:30]=3[N:29]=[CH:28][CH:27]=[CH:26]4)[CH:16]=2)=[CH:11][CH:10]=1)=[O:5])C.[Li+].[OH-]>C1COCC1>[CH3:37][S:34]([C:31]([C:23]1[CH:24]=[C:25]2[C:30](=[C:21]([C:17]3[CH:16]=[C:15]([C:12]4[CH:11]=[CH:10][C:9]([CH:7]5[CH2:8][CH:6]5[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=4)[CH:20]=[CH:19][CH:18]=3)[CH:22]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)([CH3:33])[CH3:32])(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69373788HCID 69373788, compound

Product 1

HCID 10345293HCID 10345293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{3′[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl 4-yl}-cyclopropanecarboxylic acid ethyl ester (1.0 eq.) from Step 1, in THF:MEOH (2:1; 0.2M) was added aqueous LiOH (2M; 0.2.0 eq.). The mixture was stirred for 12 h at rt, quenched with HCl 10% and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Crystallization in Hex:EtOAc afforded the title compound as a white solid. 1H NMR (400 MD, acetone-d6): δ 8.96 (dd, 1H), 8.50 (dd, 1H), 8.32 (d, 1H), 8.24 (d, 1H), 8.03 (t, 1H), 7.73–7.68 (m, 4H), 7.63–7.59 (m, 2H), 7.32 (d, 2H), 2.75 (s, 3H), 2.53 (m, 1H), 2.03 (s, 6H), 1.97 (m, 1H), 1.56 (m, 1H), 1.46 (m, 1H).

Workup

  1. customquenched with HCl 10%
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrystallization in Hex

Sources & evidence

ORD record
ord-294d3505346e4a43b1673b3acf52afdb
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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