Ammonium Hydroxide → HCID 21031295, compound

HRID 1829820Notes

Reaction equation

HRID 1829820 reaction equation
[OH:1][C@@H:2]([CH3:26])[C@@H:3]([N:16]1[CH:20]=[C:19]([C:21]([O:23]CC)=O)[N:18]=[CH:17]1)[CH2:4][S:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[OH-].[NH4+:28]>COCCOC>[C:6]1([S:5][CH2:4][C@H:3]([N:16]2[CH:20]=[C:19]([C:21]([NH2:28])=[O:23])[N:18]=[CH:17]2)[C@@H:2]([OH:1])[CH3:26])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69527991HCID 69527991, compound

Product 1

HCID 21031295HCID 21031295, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 1-{(1R,2S)-2-hydroxy-1-[(1-naphthylthio)methyl]propyl}-1H-imidazole-4-carboxylate (0.18 g), 28% ammonium hydroxide (5 mL) and 1,2-dimethoxyethane (10 mL) was heated at 100° C. in the stainless steel bottle for 24 hours. After cooling, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (gradient elution; 15:1 to 10:1 chloroform-methanol) to give 1-[(2R,3S)-1-(1-naphthylthio)-3-hydroxy-2-butyl]imidazol-4-carboxamide. The product was dissolved in MeOH (5 mL) and treated with a solution of 4 N hydrogen chloride in ethyl acetate (1 mL). The mixture was concentrated in vacuo and the residue was recrystallized from 5:1 ethyl acetate-methanol (6 mL) to give 1-{(1R,2S)-2-hydroxy-1-[(1-naphthylthio)methyl]propyl}-1H-imidazole-4-carboxamide hydrochloride (103) (0.11 g).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (gradient elution; 15:1 to 10:1 chloroform-methanol)

Sources & evidence

ORD record
ord-3e6643ec75e74c6abb697e0d00db8679
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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