1,2-Dimethoxyethane → HCID 86595163, compound

HRID 1829818Notes

Reaction equation

HRID 1829818 reaction equation
[OH:1][C@@H:2]([CH3:26])[C@H:3]([N:16]1[CH:20]=[C:19]([C:21](OCC)=[O:22])[N:18]=[CH:17]1)[CH2:4][O: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].CO[CH2:31][CH2:32]OC>>[CH2:31]([C:17]1[N:16]([C@H:3]([CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)[C@@H:2]([OH:1])[CH3:26])[CH:20]=[C:19]([C:21]([NH2:28])=[O:22])[N:18]=1)[CH3:32]

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 14923Ammonium HydroxideHCID 69527869HCID 69527869, compound

Product 1

HCID 86595163HCID 86595163, compound

Procedure

A mixture of ethyl 1-{(1R,2S)-2-hydroxy-1-[(2-naphthyloxy)methyl]propyl}-1H-imidazole-4-carboxylate (0.25 g), 28% ammonium hydroxide (14 mL) and 1,2-dimethoxyethane (7 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; 20:1 to 10:1 chloroform-methanol) to give the product, which was recrystallized from 5:1 ethyl acetate-ethanol (6 mL) to give ethyl 1-{(1R,2S)-2-hydroxy-1-[(2-naphthyloxy)methyl)propyl}-1H-imidazole-4-carboxamide (0.12 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; 20:1 to 10:1 chloroform-methanol)
  4. customto give the product, which
  5. customwas recrystallized from 5:1 ethyl acetate-ethanol (6 mL)

Sources & evidence

ORD record
ord-6504ac116b5144cba9672b5ab8d14c8a
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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