Lithium hydroxide, monohydrate → HCID 59468917, compound

HRID 1717199Notes

Reaction equation

HRID 1717199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@:19]([CH3:32])([C:28]([O:30]C)=[O:29])[CH2:18][CH2:17]2)=[CH:12][C:11]=1[O:33][CH3:34].O[Li].O>CO.O>[CH3:27][C:24]([O:23][C:21]([N:20]1[C@@H:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[C:11]([O:33][CH3:34])[CH:12]=2)[CH2:17][CH2:18][C@@:19]1([CH3:32])[C:28]([OH:30])=[O:29])=[O:22])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59468927HCID 59468927, compound

Product 1

HCID 59468917HCID 59468917, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(1,1-dimethylethyl) 2-methyl (2S,5R)-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-2-methyl-1,2-pyrrolidinedicarboxylate (D59, 160 mg, 0.34 mmol) in MeOH (1 ml) was added a solution of LiOH.H2O (29 mg, 0.68 mmol) in H2O (0.5 ml) and the mixture was heated in a microwave synthesizer for 70 min at 100° C. After evaporation of methanol, the aqueous phase was acidified to pH 3.5/4 with a solution of citric acid and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated affording the title compound (white solid, 150 mg, 97%); Rt (HPLC): 5.89 min. MS: (ES/−) m/z: 482 [M+Na] C25H30FNO6 requires 459.

Workup

  1. customAfter evaporation of methanol
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-eaa095ac501d44f8bcea1f946425a303
Source dataset
uspto-grants-2010_09
Patent number
US07803833B2

Reaction notes

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