Lithium Hydroxide → HCID 68866177, compound

HRID 1725999Notes

Reaction equation

HRID 1725999 reaction equation
C([O:8][C:9](=[O:35])[CH2:10][CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])(=[O:27])=[O:26])[C:15]=1[C:16]([O:18][CH3:19])=[O:17])C1C=CC=CC=1.[Li+].[OH-]>CO.[OH-].[OH-].[Pd+2]>[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[S:25]([NH:24][C:20]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:35])=[O:8])[CH:23]=[CH:22][CH:21]=1)(=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68864629HCID 68864629, compound

Product 1

HCID 68866177HCID 68866177, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 510D (9.84 g, 19.77 mmol) in methanol (150 mL) was added to Pd(OH)2 (1.97 g). The suspension was shaken in a reactor pressurized with 60 psi of H2 at 25° C. for 24 hours, filtered, and concentrated. The concentrate was dissolved in 4:1 methanol/H2O (200 mL), treated with LiOH (1.38 g, 57.66 mmol), stirred for 18 hours, quenched with 1N HCl (100 mL), and concentrated. The remaining solution was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated to provide desired product (7.80 g, 96%). MS (ESI(+)) m/e 427 (M+NH4)+, 432 (M+Na)+; MS (ESI(−)) m/e 408 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 11.97 (br s, 1H), 10.05 (br s, 1H), 7.68 (m, 2H), 7.41 (dd, 1H), 7.31 (t, 2H), 7.15 (d, 1H), 7.02 (d, 1H), 3.66 (s, 3H), 2.53 (m, 2H), 2.17 (m, 2H), 1.44 (m, 4H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in 4:1 methanol/H2O (200 mL)
  4. stirringstirred for 18 hours
  5. customquenched with 1N HCl (100 mL)
  6. concentrationconcentrated
  7. extractionThe remaining solution was extracted with ethyl acetate (2×100 mL)
  8. washThe combined extracts were washed with brine (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-843c48c06d3c4c1ba51956fc069bd3cc
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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