Potassium Carbonate → HCID 70651309, compound

HRID 1426056Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:18][C:17]3=[O:33])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:40]1[CH2:47][CH2:46][CH2:45][C@@H:41]1[C:42]([NH2:44])=[O:43].C([O-])(O)=O.[Na+]>CS(C)=O>[OH:32][C:29]([CH3:31])([CH3:30])[CH2:28][C@@:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:18][C:17](=[O:33])[N:16]([C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:40]4[CH2:47][CH2:46][CH2:45][C@@H:41]4[C:42]([NH2:44])=[O:43])=[N:7][CH:6]=3)=[CH:9][CH:10]=2)[CH3:15])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-{(S)-1-[4-(6-fluoro-pyridin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-[1,3]oxazinan-2-one (165 mg), potassium carbonate (76 mg), D-prolinamide (125 mg), and dimethyl sulfoxide (2 mL) was stirred at 100° C. overnight. After cooling to room temperature, aqueous NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane. The combined extracts were concentrated and the residue was purified by HPLC on reversed phase (water/methanol) to give the title compound. Yield: 85 mg (43% of theory); Mass spectrum (ESI+): m/z=543 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe resulting mixture was extracted with dichloromethane
concentrationThe combined extracts were concentrated
customthe residue was purified by HPLC on reversed phase (water/methanol)

Sources & evidence

ORD record: ord-54ca13718d5744f48bd1d02cfd7733a1
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933072B2

Reaction notes

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