Hydrochloric Acid → HCID 178464705, compound

HRID 480479Notes

Reaction equation

HRID 480479 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]([O:42]C)=O)[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl.O[C:48](C1C=C2C(=CC=1)C=C(C(O)=O)C=C2)([C:52]1[N:53]=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)C(C)C.Cl.C(N)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.O.CO>[CH2:52]([NH:53][C:40]([C:35]1[CH:34]=[CH:33][C:32]2[C:37](=[CH:38][CH:39]=[C:30]([C:2]([OH:1])([C:6]3[N:7]=[CH:8][NH:9][CH:10]=3)[CH:3]([CH3:4])[CH3:5])[CH:31]=2)[CH:36]=1)=[O:42])[CH3:48]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 187691016-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acidHCID 22285069methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate

Product 1

HCID 178464705HCID 178464705, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (14.0 g) in THF (140 mL) was added methanol (30 mL) and 4N-NaOH (30 mL) at 60° C. The mixture was stirred for 2 h, neutralized with conc.HCl. The mixture was concentrated, diluted with water and extracted with ethyl acetate. The extract was concentrated to give crude mixture of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid. To a solution of the crude mixture was added ethylamine hydrochloride (2.41 g), 1-hydroxybenzotriazole (4.53 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.67 g) under ice cooling. The mixture was stirred at room temperature for 20 h, diluted with water and extracted with ethyl acetate. The extract was concentrated and purified by column chromatography (eluent; hexane:THF=1:2) followed by crystallization from hexane-ethyl acetate to give the titled compound (12.0 g) as a colorless powder.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. customto give crude
  6. stirringThe mixture was stirred at room temperature for 20 h
  7. extractionextracted with ethyl acetate
  8. concentrationThe extract was concentrated
  9. custompurified by column chromatography (eluent; hexane:THF=1:2)
  10. customfollowed by crystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-b242e89baaea40a4abbd83616ede2079
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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