1-Hydroxybenzotriazole → (4R)-4-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 1643265Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34](O)=[O:35])=[CH:27][C:26]=1[CH3:39].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34]([NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[O:35])=[CH:27][C:26]=1[CH3:39]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (175 mg, 1.5 mmol), HOBt (810 mg, 6.0 mmol), NaHCO3 (1.0 g, 11.9 mmol) and the crude (R)-4-(4-fluoro-3-methylphenyl)-4-methoxybutanoic acid in 60 mL CH2Cl2 was added EDC.HCl (958 mg, 5.0 mmol). The mixture was stirred for 3 h at 25° C. The solvent was removed under reduced pressure and the product isolated by flash column chromatography, eluting with 10% to 60% Ethyl acetate/Hexane gradient solvent to give 208 mg of the title compound.

Workup

customThe solvent was removed under reduced pressure
customthe product isolated by flash column chromatography
washeluting with 10% to 60% Ethyl acetate/Hexane gradient solvent

Sources & evidence

ORD record: ord-2081bd4068574f2c91fef1ab69070180
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119692B2

Reaction notes

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