Potassium Carbonate → {[(3S,11aR)-8-({[(2,4-Difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl 2-(methyloxy)ethyl carbonate

HRID 875359Notes

Reaction equation

HRID 875359 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:40])[C:26]([OH:39])=[C:27]2[C:32](=[O:33])[N:31]3[C@@H:34]([CH3:37])[CH2:35][O:36][C@@H:30]3[CH2:29][N:28]2[CH:38]=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:39][C:26]1[C:25](=[O:40])[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:38][N:28]2[C:27]=1[C:32](=[O:33])[N:31]1[C@@H:34]([CH3:37])[CH2:35][O:36][C@@H:30]1[CH2:29]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21036325Iodomethyl 2-(methyloxy)ethyl carbonateHCID 66594573GSK1265744 (sodiuM salt)

Product 1

HCID 44625948{[(3S,11aR)-8-({[(2,4-Difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-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 (122 mg, 0.468 mmol), 1b (50 mg, 0.117 mmol), potassium carbonate (48 mg, 0.351 mmol), and tetrabutylammonium hydrogen sulfate (40 mg, 0.117 mmol), using a similar process to that described in example 1. 1H NMR (CDCl3) δ 10.20 (m, 1H), 8.42 (s, 1H), 7.34 (m, 1H), 6.80 (m, 2H), 5.94 (d, J=6.8 Hz, 1H), 5.87 (d, J=6.4 Hz, 1H), 5.30 (dd, J=10, 4 Hz, 1H), 4.59 (m, 2H), 4.43-4.29 (m, 5H), 3.92 (m, 3H), 3.70-3.61 (m, 3H), 3.36 (s, 3H), 1.40 (d, J=6 Hz, 3H). ES+ MS: 538 (M+1).

Sources & evidence

ORD record
ord-7ee23c94ebfe4cf6a8a1c9f82dfbed70
Source dataset
uspto-grants-2015_03
Patent number
US08981129B2

Reaction notes

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