Hydrochloric Acid → 5-Methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester hydrochloride salt

HRID 924596Notes

Reaction equation

HRID 924596 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][N:12]([O:15][CH3:16])[CH2:11][CH2:10][N:9]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:24]>C(OCC)C>[ClH:24].[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][N:12]([O:15][CH3:16])[CH2:11][CH2:10][N:9]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 867199125-Methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 867199115-Methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester hydrochloride salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester in diethyl ether was treated with gaseous hydrogen chloride to generate a white precipitate. The solid was filtered, washed with diethyl ether and dried to afford 5-methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester hydrochloride salt. To a suspension of 5-methoxy-[1,2,5]triazepane-1,2-dicarboxylic acid di-tert-butyl ester hydrochloride salt (2.5 g, 6.8 mmol) in ethyl acetate (10 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4 M, 9 ml, 36.0 mmol) at room temperature dropwise. The reaction mixture was heated at 90° C. for one hour, the solvent evaporated, the residue washed with diethyl ether and dried in vacuo. Yield: 1.4 g of 5-methoxy-[1,2,5]triazepane hydrochloride salt (compound P4.2) as a yellowish solid, this material was used without further purification.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-def5119aaf854ecdaafe39ad932e9bd8
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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