Potassium Carbonate → n-(3-((r)-3-((s)-1-(4-(1-Methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propyl)methanesulfonamide

HRID 406683Notes

Reaction equation

O[CH2:2][CH2:3][CH2:4][C@@:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH3:27])[CH:21]=3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49].C([O-])([O-])=O.[K+].[K+]>>[CH3:27][N:22]1[C:23](=[O:26])[CH:24]=[CH:25][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C@@H:12]([N:8]3[CH2:7][CH2:6][C@:5]([CH2:4][CH2:3][CH2:2][NH:51][S:48]([CH3:47])(=[O:50])=[O:49])([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[O:10][C:9]3=[O:11])[CH3:13])=[CH:15][CH:16]=2)=[CH:21]1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 72879Methanesulfonamide

HCID 59635752(R)-6-(3-hydroxypropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

HCID 131709961Jones' reagent

Product 1

HCID 59635644n-(3-((r)-3-((s)-1-(4-(1-Methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propyl)methanesulfonamide

Procedure

The title compound was prepared from (R)-6-(3-hydroxypropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one by treatment with (i) MeSO2Cl and (ii) MeSO2NH2, K2CO3. LC-MS Method 2 tR=1.095 min, m/z=524.1; 1H NMR (CDCl3) 1.30-1.41 (m, 1H), 1.52 (d, 3H), 1.71 (m, 1H), 1.87-2.07 (m, 3H), 2.09-2.20 (m, 3H), 2.22-2.32 (m, 2H), 2.88 (s, 3H), 3.06 (m, 2H), 3.60 (s, 3H), 4.32 (s, 1H), 5.65 (m, 1H), 6.67 (d, 1H), 6.94 (m, 2H), 7.11 (d, 2H), 7.25 (m, 1H), 7.27-7.40 (m, 4H), 7.53 (dd, 1H).

Sources & evidence

ORD record: ord-0a5b55d261244804b1ebb1e3558a2f05
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754076B2

Reaction notes

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