Methanol → HCID 178496238, compound

HRID 2167299Notes

Reaction equation

HRID 2167299 reaction equation
Cl.O[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]=1C(=N)OCC.Cl.[NH2:23][CH2:24][C:25]([NH:31]Cl)([CH3:30])[C:26]([O:28][CH3:29])=[O:27].CCN(CC)CC.[CH3:40][OH:41]>>[OH:41][C:40]1[C:12]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:3]=[CH:4][C:10]=1[C:11]1[NH:23][CH2:24][C:25]([CH3:30])([C:26]([O:28][CH3:29])=[O:27])[N:31]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 86659087HCID 86659087, compoundHCID 136341052HCID 136341052, compound

Product 1

HCID 178496238HCID 178496238, compoundYield 25%

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). Et3N (1 mL) was added dropwise 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 (90 mg, 25%). 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-43ba18a9dc8a411c8126d54d05c4bf57
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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