Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1360166Generated: October 29, 2026

Ethyl diazoacetate → (S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl ester

https://huagongshe.com/reaction/1360166

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl diazoacetateHCID 12192—
ReactantN-Boc-(S)-1-amino-2-propanolHCID 11789722—
CatalystRhodium acetateHCID 168478—
Solvent1,1-DichloroethaneHCID 6365—
Product(S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl esterHCID 8662190669.4%

Reaction Conditions

Temperature80 °C

Reaction Steps

1.16 g (6.61 mmol) of (S)-(2-hydroxy-propyl)-carbamic acid t-butyl ester was dissolved in 20 mL of dichloroethane, then 0.66 mL (9.84 mmol) of ethyl diazoacetate was added thereto. 57 mg (0.12 mmol) of rhodium acetate was dropwise added thereto, and then heated to at 80° C. for 2 hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 1.2 g (4.59 mmol) of the title compound in a yield of 69%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07879848B2
Source datasetuspto-grants-2011_02
ORD IDord-cb3a68af140f42c8a17e551722efc526
Source noteuspto-grants-2011_02