Potassium Carbonate → Phenylmethyl ({[({[(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 875362Notes

Reaction equation

HRID 875362 reaction equation
I[CH2:2][O:3][C:4]([O:6][CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:5].[Na].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH2:27][NH:28][C:29]([C:31]1[C:32](=[O:47])[C:33]([OH:46])=[C:34]2[C:39](=[O:40])[N:38]3[C@@H:41]([CH3:44])[CH2:42][O:43][C@@H:37]3[CH2:36][N:35]2[CH:45]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH2:27][NH:28][C:29]([C:31]1[C:32](=[O:47])[C:33]([O:46][CH2:2][O:3][C:4]([O:6][CH2:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[O:5])=[C:34]2[C:39](=[O:40])[N:38]3[C@@H:41]([CH3:44])[CH2:42][O:43][C@@H:37]3[CH2:36][N:35]2[CH:45]=1)=[O:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66594573GSK1265744 (sodiuM salt)HCID 86709911Phenylmethyl ({[(iodomethyl)oxy]carbonyl}oxy)acetate

Product 1

HCID 44626148Phenylmethyl ({[({[(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 phenylmethyl ({[(iodomethyl)oxy]carbonyl}oxy)acetate (819 mg, 2.34 mmol), 1b (500 mg, 1.17 mmol), potassium carbonate (485 mg, 3.51 mmol), and tetrabutylammonium hydrogen sulfate (397 mg, 1.17 mmol), using a similar process to that described in example 1. 1H NMR (CDCl3) δ 10.18 (m, 1H), 8.36 (s, 1H), 7.34-7.27 (m, 6H), 6.76 (m, 2H), 5.98 (d, J=6.8 Hz, 1H), 5.85 (d, J=6.4 Hz, 1H), 5.27 (dd, J=10, 4 Hz, 1H), 5.15 (s, 2H), 4.66 (s, 2H), 4.60 (m, 2H), 4.39-4.23 (m, 3H), 3.88 (m, 1H), 3.64 (m, 1H), 1.35 (d, J=6.4 Hz, 3H). ES+ MS: 628 (M+1).

Sources & evidence

ORD record
ord-18686304c27b444c99e4d2cdfe4bfcda
Source dataset
uspto-grants-2015_03
Patent number
US08981129B2

Reaction notes

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