Potassium Carbonate → Methyl ({[({[(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)oxy]carbonyl}oxy)acetate

HRID 875363Notes

Reaction equation

HRID 875363 reaction equation
I[CH2:2][O:3][C:4]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5].[Na].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[CH2:21][NH:22][C:23]([C:25]1[C:26](=[O:41])[C:27]([OH:40])=[C:28]2[C:33](=[O:34])[N:32]3[C@@H:35]([CH3:38])[CH2:36][O:37][C@@H:31]3[CH2:30][N:29]2[CH:39]=1)=[O:24].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[CH2:21][NH:22][C:23]([C:25]1[C:26](=[O:41])[C:27]([O:40][CH2:2][O:3][C:4]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5])=[C:28]2[C:33](=[O:34])[N:32]3[C@@H:35]([CH3:38])[CH2:36][O:37][C@@H:31]3[CH2:30][N:29]2[CH:39]=1)=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66594573GSK1265744 (sodiuM salt)HCID 86688409HCID 86688409, compound

Product 1

HCID 44626085Methyl ({[({[(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)oxy]carbonyl}oxy)acetate

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

The title compound was prepared from methyl ({[(iodomethyl)oxy]carbonyl}oxy)acetate (103 mg, 0.374 mmol), 1b (80 mg, 0.187 mmol), potassium carbonate (78 mg, 0.5621 mmol), and tetrabutylammonium hydrogen sulfate (64 mg, 0.187 mmol), using a similar process to that described in example 1. 1H NMR (CDCl3) δ 10.20 (m, 1H), 8.39 (s, 1H), 7.33 (m, 1H), 6.78 (m, 2H), 6.00 (d, J=6.8 Hz, 1H), 5.88 (d, J=6.8 Hz, 1H), 5.30 (dd, J=10, 4 Hz, 1H), 4.63-4.58 (m, 4H), 4.43-4.28 (m, 4H), 3.93 (m, 1H), 3.73 (s, 2H), 3.66 (m, 1H), 1.38 (d, J=6 Hz, 3H). ES+ MS: 552 (M+1).

Sources & evidence

ORD record
ord-fe6d58c4bda1474793fc92f82022e89f
Source dataset
uspto-grants-2015_03
Patent number
US08981129B2

Reaction notes

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