Potassium Carbonate → HCID 70651309, compound

HRID 1528666Notes

Reaction equation

HRID 1528666 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

6

Reactant 4

HCID 11430Potassium CarbonateHCID 447554Prolinamide, D-HCID 516892Sodium BicarbonateHCID 67997620HCID 67997620, compound

Product 1

HCID 70651309HCID 70651309, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-{(S)-1-[4-(6-fluoro-pyridin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-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° (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

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. concentrationThe combined extracts were concentrated
  3. customthe residue was purified by HPLC on reversed phase (water/methanol)

Sources & evidence

ORD record
ord-67493af6ecaa4dc49b4a20f67d490f4c
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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