Hydrochloric Acid → HCID 178485272, compound

HRID 480465Notes

Reaction equation

HRID 480465 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](OC)=[O:41])[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.OC(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.CN.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.O.CO>[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]([NH:53][CH3:52])=[O:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:4])[CH3:5]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 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 178485272HCID 178485272, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (1.80 g) in THF (20 mL) was added methanol (4 mL) and 4N-NaOH (20 mL) at 50° C. The mixture was stirred for 90 min, 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 methylamine in THF (2.0M:3.50 mL), 1-hydroxybenzotriazole (536 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (671 mg) 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 (1.55 g) as a pale yellow 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-ff848df50c71442a890aa0e566efe010
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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