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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2114900Generated: October 31, 2026

Phosgene → (S)-[3-(1-cyclopropyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-yl)-2-oxo-oxazolidin-5-ylmethyl]-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/2114900

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhosgeneHCID 6371—
ReactantTriethylamineHCID 8471—
Reactant(R)-[3-(1-cyclopropyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl esterHCID 69274192—
SolventDichloromethaneHCID 6344—
Product(S)-[3-(1-cyclopropyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-yl)-2-oxo-oxazolidin-5-ylmethyl]-carbamic acid tert-butyl esterHCID 69274116—

Reaction Steps

Phosgene (20% solution in toluene, 0.754 ml, 7.71 mmol) is added to (R)-[3-(1-cyclopropyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester (0.390 g, 1.03 mmol) and triethylamine (0.711 ml, 5.13 mmol) in dichloromethane (5 ml) at 0° C. and stirred for 30 minutes. The mixture is diluted with dichloromethane, washed with water and brine, dried (Na2SO4) and evaporated to give the title compound as a yellow solid. HPLC r.t. 4.96 min; MS for C20H24FN3O5 m/z 406 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07435751B2
Source datasetuspto-grants-2008_10
ORD IDord-91a8f44e63354f92b888a91af68d4688
Source noteuspto-grants-2008_10