Hydrochloric Acid → [2-((S)-1-aminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazol-4-yl]methanol dihydrochloride

HRID 243253Notes

Reaction equation

HRID 243253 reaction equation
C(OC([NH:8][C@H:9]([C:11]1[N:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[C:19]([CH2:20][O:21]C(=O)C)=[C:18]([F:25])[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10])=O)(C)(C)C.[ClH:32]>CO.O1CCOCC1>[ClH:32].[ClH:32].[NH2:8][C@H:9]([C:11]1[N:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[C:19]([CH2:20][OH:21])=[C:18]([F:25])[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157763Acetic acid 2-((S)-1-tert-butoxycarbonylaminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazol-4-ylmethyl ester

Product 1

HCID 68157540[2-((S)-1-aminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazol-4-yl]methanol dihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of acetic acid 2-((S)-1-tert-butoxycarbonylaminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazol-4-ylmethyl ester (190 mg, 0.44 mmol) in methanol (2 mL) was added HCl in dioxane (4N, 5 mL) and the reaction stirred at RT for 2 h. The reaction mixture was concentrated in vacuo to give the title compound as a beige solid (159 mg, 100%). LCMS (Method C): RT=1.61 min, [M+H]+=372.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-412f7589e62e4cca9c9399edd7428139
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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