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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1429362Generated: November 1, 2026

Ethyl Acetate → Methyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoate

https://huagongshe.com/reaction/1429362

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 2-(bromomethyl)benzoateHCID 2734813—
Reactanttert-Butyl 3-(4-bromophenyl)-1-hydroxypropan-2-ylcarbamateHCID 57594209—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoateHCID 6738243134%

Reaction Steps

To a solution of compound 3f (6.6 g, 20 mmol) in dry THF (100 mL) was added NaH (60%, 960 mg, 24 mmol) in small portions at 0° C. and stirred for 1 hr. Then compound 3b (5 g, 22 mmol) in THF (50 mL) was added dropwise, and the reaction mixture was allowed to stir at rt overnight. The reaction was quenched with water and extracted with EA (2×100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by CC eluting with PE:EA=9:1 to give 3g as a white solid (3.2 g, 34% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08940722B2
Source datasetuspto-grants-2015_01
ORD IDord-1a31c6c7eb334efba815538644671012
Source noteuspto-grants-2015_01