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-{[2-(methyloxy)ethyl]oxy}ethyl carbonate

HRID 875360Notes

Reaction equation

HRID 875360 reaction equation
[C:1](=[O:13])([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[O:2][CH2:3]I.[Na].[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[CH2:23][NH:24][C:25]([C:27]1[C:28](=[O:43])[C:29]([OH:42])=[C:30]2[C:35](=[O:36])[N:34]3[C@@H:37]([CH3:40])[CH2:38][O:39][C@@H:33]3[CH2:32][N:31]2[CH:41]=1)=[O:26].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1](=[O:13])([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])[O:2][CH2:3][O:42][C:29]1[C:28](=[O:43])[C:27]([C:25]([NH:24][CH2:23][C:17]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=2[F:15])=[O:26])=[CH:41][N:31]2[C:30]=1[C:35](=[O:36])[N:34]1[C@@H:37]([CH3:40])[CH2:38][O:39][C@@H:33]1[CH2:32]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66594573GSK1265744 (sodiuM salt)HCID 86055900Iodomethyl 2-{[2-(methyloxy)ethyl]oxy}ethyl carbonate

Product 1

HCID 44625950{[(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-{[2-(methyloxy)ethyl]oxy}ethyl carbonate

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

The title compound was prepared from iodomethyl 2-{[2-(methyloxy)ethyl]oxy}ethyl carbonate (57 mg, 0.187 mmol), 1b (40 mg, 0.094 mmol), potassium carbonate (39 mg, 0.281 mmol), and tetrabutylammonium hydrogen sulfate (32 mg, 0.094 mmol), using a similar process to that described in example 1. 1H NMR (CDCl3) δ 10.21 (m, 1H), 8.44 (s, 1H), 7.32 (m, 1H), 6.81 (m, 2H), 5.93 (d, J=6.4 Hz, 1H), 5.83 (d, J=6.4 Hz, 1H), 5.30 (dd, J=10, 3.6 Hz, 1H), 4.59 (m, 2H), 4.43-4.27 (m, 5H), 3.93 (m, 1H), 3.77-3.61 (m, 5H), 3.52 (m, 2H), 3.35 (s, 3H), 1.38 (d, J=6.4 Hz, 3H). ES+ MS: 582 (M+1).

Sources & evidence

ORD record
ord-5e82f7b6e0854a269c0e0920e170a377
Source dataset
uspto-grants-2015_03
Patent number
US08981129B2

Reaction notes

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