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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 612364Generated: October 30, 2026

Triethylamine → 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

https://huagongshe.com/reaction/612364

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantCysteamine HydrochlorideHCID 9082—
Reactanttert-butyl N-((2S)-1-oxopropan-2-yl)carbamateHCID 7015728—
SolventDimethylformamideHCID 6228—
Product1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 7023103—

Reaction Steps

6.82 g (60 mmoles) of cysteamine hydrochloride is dissolved in 50 ml of dimethylformamide, and the solution is neutralized with 8.4 ml of triethylamine. The solution is mixed with a solution of crude Boc-L-alaninal obtained by oxidizing 8.75 g (50 mmoles) of Boc-alaninol in 50 ml of dimethylformamide, and mixture is stirred overnight at room temperature. The solvent is distilled off under reduced pressure, the formed crystals are dissolved in ethyl acetate, the solution is washed with 10% citric acid and saturated aqueous sodium bicarbonate, and the ethyl acetate layer is dried. The solvent is distilled off under reduced pressure to obtain 4.93 g (42.6%) of the desired compound 9-A as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06004934
Source datasetuspto-grants-1999_12
ORD IDord-65bace1748e2495f9e95af766a031d95
Source noteuspto-grants-1999_12