Hydrochloric Acid → 1-((1-Methoxy-4-methyl-1-oxopentan-2-yl)amino)-1-oxopent-4-yn-2-aminium chloride

HRID 627577Notes

Reaction equation

HRID 627577 reaction equation
C(OC([NH:8][CH:9]([CH2:22][C:23]#[CH:24])[C:10]([NH:12][CH:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[O:11])=O)(C)(C)C.[ClH:25].O1CCOCC1>C(Cl)Cl>[Cl-:25].[CH3:17][O:16][C:14](=[O:15])[CH:13]([NH:12][C:10](=[O:11])[CH:9]([NH3+:8])[CH2:22][C:23]#[CH:24])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90010236Methyl 2-(2-((tert-butoxycarbonyl)amino)pent-4-ynamido)-4-methylpentanoate

Product 1

HCID 900103681-((1-Methoxy-4-methyl-1-oxopentan-2-yl)amino)-1-oxopent-4-yn-2-aminium chlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 1 (10.55 g: 31 mmol) in DCM (100 mL) was treated with 4M HCl in dioxane (78 mL; 0.31 mol) and stirred at room temperature for 3 h while monitoring the disappearance of the starting material by TLC. The solvent was removed on the rotary evaporator and the residue was treated with ether and then concentrated to give 2 as an off white solid (8.3 g; 96% yield).

Workup

  1. customThe solvent was removed on the rotary evaporator
  2. additionthe residue was treated with ether
  3. concentrationconcentrated
  4. customto give 2 as an off white solid (8.3 g; 96% yield)

Sources & evidence

ORD record
ord-1254d62114c142c2a9d0b8dbb023b667
Source dataset
uspto-grants-2016_04
Patent number
US09309284B2

Reaction notes

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