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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 726424Generated: October 25, 2026

Methanol → (S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

https://huagongshe.com/reaction/726424

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
ReactantL-N-Cbz-3-N-Boc-Amino-alanineHCID 2756240—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 6344—
Product(S)-Methyl 2-N-Cbz-3-N-Boc-propanoateHCID 10831821—

Reaction Steps

The product (0.867 g) obtained in the above (2) is dissolved in dichloromethane (15 ml), and thereto are added methanol (1.5 ml), 4-dimethylaminopyridine (34 mg) and WSC.HCl (0.633 g) under ice-cooling. The mixture is stirred under ice-cooling for two hours, and then stirred at room temperature for 12 hours. The mixture is concentrated under reduced pressure to the volume of about 5 ml, and the residue is poured into water. The mixture is extracted three time with ethyl acetate, and the organic layer is washed 1N HCl (twice), a saturated aqueous sodium hydrogen carbonate solution (twice), and with a saturated brine (twice), and then dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (0.875 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05707994
Source datasetuspto-grants-1998_01
ORD IDord-0a24c82ff362497c92f30afb38e000cd
Source noteuspto-grants-1998_01