Potassium Carbonate → {[(4R,12aS)-9-({[(2,4-Difluorophenyl)methyl]amino}carbonyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazin-7-yl]oxy}methyl 2-(methyloxy)ethyl carbonate

HRID 1511535Notes

Reaction equation

HRID 1511535 reaction equation
[C:1](=[O:10])([O:5][CH2:6][CH2:7][O:8][CH3:9])[O:2][CH2:3]I.[Na].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH:21][C:22]([C:24]1[C:25](=[O:41])[C:26]([OH:40])=[C:27]2[C:36](=[O:37])[N:35]3[C@@H:30]([O:31][CH2:32][CH2:33][C@H:34]3[CH3:38])[CH2:29][N:28]2[CH:39]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1](=[O:10])([O:5][CH2:6][CH2:7][O:8][CH3:9])[O:2][CH2:3][O:40][C:26]1[C:25](=[O:41])[C:24]([C:22]([NH:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=2[F:12])=[O:23])=[CH:39][N:28]2[C:27]=1[C:36](=[O:37])[N:35]1[C@@H:30]([O:31][CH2:32][CH2:33][C@H:34]1[CH3:38])[CH2:29]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21036325Iodomethyl 2-(methyloxy)ethyl carbonateHCID 67179015(4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide sodium salt

Product 1

HCID 44603098{[(4R,12aS)-9-({[(2,4-Difluorophenyl)methyl]amino}carbonyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazin-7-yl]oxy}methyl 2-(methyloxy)ethyl carbonate

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

The title compound was prepared from iodomethyl 2-(methyloxy)ethyl carbonate (59 mg, 0.227 mmol) (prepared in a similar manner to example 1), (4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2′:4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide sodium salt (50 mg, 0.113 mmol), potassium carbonate (47 mg, 0.340 mmol), and tetrabutylammonium hydrogen sulfate (39 mg, 0.113 mmol), using a similar process to that described in example 1. 1H NMR (CDCl3) δ 10.32 (m, 1H), 8.37 (s, 1H), 7.31 (m, 1H), 6.77 (m, 2H), 5.83 (m, 2H), 5.16 (m, 1H), 4.92 (m, 1H), 4.57 (d, J=6 Hz, 2H), 4.29-4.23 (m, 3H), 4.16 (m, 1H), 3.93 (m, 2H), 3.62-3.57 (m, 2H), 3.32 (s, 3H), 2.13 (m, 1H), 1.46 (m, 1H), 1.30 (d, J=7.2 Hz, 3 H). ES+MS: 552 (M+1).

Sources & evidence

ORD record
ord-57568dff65fa4c4caf20240b6a9dc4d0
Source dataset
uspto-grants-2012_07
Patent number
US08217034B2

Reaction notes

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