Ammonium Hydroxide → HCID 69527314, compound

HRID 1829819Notes

Reaction equation

HRID 1829819 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[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[NH4+:28]>COCCOC>[OH:1][C@@H:2]([CH3:26])[C@@H:3]([N:16]1[CH:20]=[C:19]([C:21]([NH2:28])=[O:23])[N:18]=[CH:17]1)[CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69526912HCID 69526912, compound

Product 1

HCID 69527314HCID 69527314, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 1-{(1R,2S)-2-hydroxy-1-[(2-naphthylthio)methyl]propyl}-1H-imidazole-4-carboxylate (0.18 g), 28% ammonium hydroxide (20 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 (elution; 10:1 chloroform-1% ammonium hydroxide/methanol) to give the product, which was recrystallized from 3:7 n-hexane-ethyl acetate (10 mL) to give 1-{(1R,2S)-2-hydroxy-1-[(2-naphthylthio)methyl]propyl}-1H-imidazole-4-carboxamide (102) (90 mg).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (elution; 10:1 chloroform-1% ammonium hydroxide/methanol)
  4. customto give the product, which
  5. customwas recrystallized from 3:7 n-hexane-ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-2b05a9a14aed4fd5a5b3c877a359170a
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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