Water → HCID 58065441, compound

HRID 1964520Notes

Reaction equation

HRID 1964520 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][C@H:10]([CH3:45])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[CH:44]=[CH:43][C:37]([C:38](OCC)=[O:39])=[CH:36][N:35]=3)=[CH:31][CH:30]=2)[CH:15]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:17]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][C@H:10]([CH3:45])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[N:35]=[CH:36][C:37]([CH2:38][OH:39])=[CH:43][CH:44]=3)=[CH:31][CH:30]=2)[CH:15]=[C:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66891470HCID 66891470, compound

Product 1

HCID 58065441HCID 58065441, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (12 mg, 0.316 mmol) was suspended in tetrahydrofuran (2 mL). Ethyl 6-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)nicotinate (56.0 mg, 0.102 mmol) synthesized in Example (11c) was dissolved in tetrahydrofuran (2 mL), followed by dropwise addition at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 30 minutes, water (12 μL) and an aqueous sodium hydroxide solution (5M, 48 μl) were added dropwise slowly and sequentially. After filtration through Celite, the solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%) to afford the desired compound (33 mg, yield 64%) as a pale yellow solid.

Workup

  1. additionfollowed by dropwise addition at 0° C. under nitrogen atmosphere
  2. filtrationAfter filtration through Celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%)

Sources & evidence

ORD record
ord-361cdaa5293646248d029446e8cef921
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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