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

HRID 2201133Notes

Reaction equation

HRID 2201133 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-80e2d7b5c778497787f9d742e9d37755
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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