Carbonic acid--N,N-diethylethanamine (1/2) → (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide

HRID 84901Notes

Reaction equation

HRID 84901 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([NH:17]C(=O)OC(C)(C)C)[C:14]([NH2:16])=[O:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>Cl.O1CCOCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][C@@H:13]([NH2:17])[C:14]([NH2:16])=[O:15])=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 67515389(R)-tert-butyl 3-(4-(1H-imidazol-1-yl)phenyl)-1-amino-1-oxopropan-2-ylcarbamate

Product 1

HCID 67516322(R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of ((R)-tert-butyl 3-(4-(1H-imidazol-1-yl)phenyl)-1-amino-1-oxopropan-2-ylcarbamate (250 mg, 0.757 mmol) in 4M HCl in dioxane (4 mL) and 6N HCl (4 mL) was stirred at room temperature for 30 min. It was then concentrated in vacuo. The residue was dissolved in MeOH (10 mL), MP-carbonate resin (1.00 g, ca. 3 mmol/g, 3.00 mmol) was added. After swirling and standing for 2 h, the resin was filtered off. The filtrate was concentrated in vacuo to give (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-aminopropanamide as free base (100 mg).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. filtrationthe resin was filtered off
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-92f89a72cbde4d3d83b857a718ca1140
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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