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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1618366Generated: October 29, 2026

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

https://huagongshe.com/reaction/1618366

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantGSK1265744 (sodiuM salt)HCID 66594573—
ReactantPhenylmethyl ({[(iodomethyl)oxy]carbonyl}oxy)acetateHCID 86709911—
CatalystTetrabutylammonium hydrogen sulfateHCID 94433—
ProductPhenylmethyl ({[({[(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)acetateHCID 44626148—

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08765965B2
Source datasetuspto-grants-2014_07
ORD IDord-7cac200b17e64ec4b4342114db5de415
Source noteuspto-grants-2014_07