Triethylamine → HCID 178496236, compound

HRID 2167295Notes

Reaction equation

HRID 2167295 reaction equation
Cl.[OH:2][C:3]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:11]=[CH:10][C:4]=1[C:5](=[NH:9])OCC.Cl.N[CH2:24][C:25]([NH:31]Cl)([CH3:30])[C:26]([O:28][CH3:29])=[O:27].CCN(CC)CC>CO>[OH:2][C:3]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:11]=[CH:10][C:4]=1[C:5]1[NH:9][CH2:24][C:25]([CH3:30])([C:26]([O:28][CH3:29])=[O:27])[N:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86659087HCID 86659087, compoundHCID 136341052HCID 136341052, compound

Product 1

HCID 178496236HCID 178496236, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)benzimidate hydrochloride (0.35 g, crude, ˜1.0 mmol) in MeOH (10 mL) was added methyl 3-amino-2-(chloroamino)-2-methylpropanoate hydrochloride (0.24 g, crude, ˜1.0 mmol) followed by dropwise addition of Et3N (1 mL) at 0° C. The resulting solution was refluxed overnight. The solvent was evaporated under vacuum and the residue was purified by prep-HPLC to obtain the title compound as colorless oil (175 mg, 50%). LC-MS (ES, m/z): 353 [M+H]+.

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-cd2db103671c48509c024990e4d6240c
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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