Water → HCID 58065449, compound

HRID 1964547Notes

Reaction equation

HRID 1964547 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][C@H:10]([CH3:43])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[O:35][CH:36]([C:39](OC)=[O:40])[CH2:37][N:38]=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]([CH3:43])[O:11][C:12]1[CH:13]=[C:14]([C:29]2[NH:33][C:32]([C:34]3[O:35][CH:36]([CH2:39][OH:40])[CH2:37][N:38]=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:27])=[O:26])=[CH:23][CH:24]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58065478HCID 58065478, compound

Product 1

HCID 58065449HCID 58065449, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (17.0 mg, 0.448 mmol) was suspended in tetrahydrofuran (2 mL). Methyl 2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazole-5-carboxylate (77.0 mg, 0.146 mmol) synthesized in Example (27b) 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 (17 μL) and an aqueous sodium hydroxide solution (5M, 68 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 (54.1 mg, yield 74%) as a white 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-e5042a2688d647158d38e8e019a68707
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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