Dimethylamine → HCID 10944665, compound

HRID 500176Notes

Reaction equation

HRID 500176 reaction equation
[CH:1]([N:4](CC)[CH:5](C)C)(C)C.[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH:22]([CH3:24])[CH3:23])[C:19](O)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].Cl.CN(C)CCCN=C=NCC.CNC>C1COCC1.C(Cl)Cl>[CH3:1][N:4]([CH3:5])[C:19]([C@@H:18]([NH:17][C:15](=[O:16])[O:14][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:22]([CH3:24])[CH3:23])=[O:20]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10944665HCID 10944665, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N,N-Diisopropylethylamine (1.0 mL, 5.74 mmol) was added to a mixture of (2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid (0.217 g, 1.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.211 g, 1.1 mmol) and dimethylamine in THF (2M, 1.0 mL) in methylene chloride (10 mL). The mixture was stirred overnight at RT. The mixture was washed with water, saturated NaHCO3 solution, brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel to give the desired product (131 mg, 53.6%).

Workup

  1. washThe mixture was washed with water, saturated NaHCO3 solution, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-a7414a6db1ab40adbb0f1029f7806e75
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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