1,4-Dioxane hydrochloride → N,N2,O,2-tetramethyl-3-oxoserinamide hydrochloride

HRID 1519659Notes

Reaction equation

HRID 1519659 reaction equation
[ClH:1].O1CCOCC1.C(O[C:13]([N:15](C)[C@:16]([CH3:25])([C:21]([NH:23][CH3:24])=[O:22])[C:17](=[O:20])[O:18][CH3:19])=O)(C)(C)C>O1CCOCC1>[ClH:1].[CH3:24][NH:23][C:21](=[O:22])[C@:16]([CH3:25])([C:17](=[O:20])[O:18][CH3:19])[NH:15][CH3:13]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86679249N2-(t-butoxycarbonyl)-N,N2,O,2-tetramethyl-3-oxoserinamide2×

Product 1

HCID 131733095N,N2,O,2-tetramethyl-3-oxoserinamide hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 4.0 mol/L-hydrochloric acid-dioxane solution (5.0 mL) was added to a dioxane (5.0 mL) solution of N2-(t-butoxycarbonyl)-N,N2,O,2-tetramethyl-3-oxoserinamide (Intermediate 8-2, 1.5 g) under ice cooling, and the mixture was stirred for 18 hours at room temperature. Then, the reaction mixture was concentrated to obtain N,N2,O,2-tetramethyl-3-oxoserinamide hydrochloride (Intermediate 9-2, white solid) (1.1 g, 98%).

Workup

  1. concentrationThen, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-5ad5578ec8e04264ab06ec65787cb171
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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