1-Hydroxybenzotriazole → HCID 178502886, compound

HRID 480466Notes

Reaction equation

HRID 480466 reaction equation
OC(C1C=C2C(=CC=1)C=C(C(O)=O)C=C2)C(C)CC1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1.[OH:43][C:44]([C:72]1[CH:73]=[C:74]2[C:79](=[CH:80][CH:81]=1)[CH:78]=[C:77]([C:82](OC)=[O:83])[CH:76]=[CH:75]2)([C:48]1[N:49]=[CH:50][N:51](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:52]=1)[CH:45]([CH3:47])[CH3:46].Cl.[CH3:87][O:88][NH2:89].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.O>[OH:43][C:44]([C:72]1[CH:73]=[C:74]2[C:79](=[CH:80][CH:81]=1)[CH:78]=[C:77]([C:82]([NH:89][O:88][CH3:87])=[O:83])[CH:76]=[CH:75]2)([C:48]1[N:49]=[CH:50][NH:51][CH:52]=1)[CH:45]([CH3:47])[CH3:46]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22285069methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoateHCID 688844966-(1-hydroxy-2-methyl-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid

Product 1

HCID 178502886HCID 178502886, compoundYield 158.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to that described in Example 9-(i), a crude mixture of 6-(1-hydroxy-2-methyl-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid was obtained by the reaction using methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (2.0 g). To a solution of the crude mixture in THF (30 mL) was added methoxyamine hydrochloride (354 mg), 1-hydroxybenzotriazole (594 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (744 mg) under ice cooling. The mixture was stirred at room temperature for 15 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 (1.90 g) as a pale yellow powder.

Workup

  1. customwas obtained by the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract was concentrated
  4. custompurified by column chromatography (eluent; hexane:THF=1:2)
  5. customfollowed by crystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-dda49dd4fe3842e7b97d726bf014d22f
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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