HCID 131735454, compound → HCID 118060967, compound

HRID 632771Notes

Reaction equation

HRID 632771 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][N:12]([C:14]2[C:18]([NH:19][C:20]([C:22]3[N:23]=[C:24]([CH3:27])[O:25][CH:26]=3)=[O:21])=[CH:17][N:16]([CH3:28])[N:15]=2)[C:11](=[O:29])[CH2:10]1)(C(C)(C)C)(C)C>C1COCC1.O>[OH:8][C@@H:9]1[CH2:13][N:12]([C:14]2[C:18]([NH:19][C:20]([C:22]3[N:23]=[C:24]([CH3:27])[O:25][CH:26]=3)=[O:21])=[CH:17][N:16]([CH3:28])[N:15]=2)[C:11](=[O:29])[CH2:10]1

Participants

4

Reactant 1

HCID 131735454HCID 131735454, compound

Product 1

HCID 118060967HCID 118060967, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-((4S)-4-((tert-butyl(dimethyl)silyl)oxy)-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-methyl-1,3-oxazole-4-carboxamide (32 mg) in THF (2.0 mL) was added 1M tetra-n-butylammonium fluoride THF solution (0.15 mL), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (10 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-56fa78c959d847f58c113fc2a470eda5
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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