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 1-methylethyl carbonate

HRID 1618362Notes

Reaction equation

HRID 1618362 reaction equation
[C:1](=[O:9])([O:5][CH:6]([CH3:8])[CH3:7])[O:2][CH2:3]I.[Na].[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[CH2:19][NH:20][C:21]([C:23]1[C:24](=[O:39])[C:25]([OH:38])=[C:26]2[C:31](=[O:32])[N:30]3[C@@H:33]([CH3:36])[CH2:34][O:35][C@@H:29]3[CH2:28][N:27]2[CH:37]=1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1](=[O:9])([O:5][CH:6]([CH3:8])[CH3:7])[O:2][CH2:3][O:38][C:25]1[C:24](=[O:39])[C:23]([C:21]([NH:20][CH2:19][C:13]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=2[F:11])=[O:22])=[CH:37][N:27]2[C:26]=1[C:31](=[O:32])[N:30]1[C@@H:33]([CH3:36])[CH2:34][O:35][C@@H:29]1[CH2:28]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15870216Iodomethyl propan-2-yl carbonateHCID 66594573GSK1265744 (sodiuM salt)

Product 1

HCID 44625949{[(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 1-methylethyl carbonate

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

The title compound was prepared from iodomethyl 1-methylethyl carbonate (140 mg, 0.574 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 10.29 (m, 1H), 8.44 (s, 1H), 7.29 (m, 1H), 6.77 (m, 2H), 5.84 (s, 2H), 5.27 (dd, J=9.6, 3.6 Hz, 1H), 4.88 (m, 1H), 4.56 (m, 2H), 4.40-4.29 (m, 3H), 3.89 (m, 1H), 3.65 (m, 1H), 1.37 (d, J=6.4 Hz, 3H) 1.26 (m, 6H). ES+ MS: 522 (M+1).

Sources & evidence

ORD record
ord-8a5f176195d44d10a21156d0121eac46
Source dataset
uspto-grants-2014_07
Patent number
US08765965B2

Reaction notes

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