Hydrochloric Acid → 4'-((R)-1-Amino-ethyl)-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester hydrochloride

HRID 1404544Notes

Reaction equation

HRID 1404544 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH:20]C(OC(C)(C)C)=O)[CH3:19])=[C:14]([F:28])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4].Cl.O1CCOCC1>>[ClH:11].[CH3:1][O:2][C:3]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([C@H:18]([NH2:20])[CH3:19])=[C:14]([F:28])[CH:13]=2)=[CH:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 161028894'-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 161029164'-((R)-1-Amino-ethyl)-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester hydrochloride

Procedure

4′-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester (350 mg, 858 μmol, step A) was added to a solution of HCl in dioxane (4N, 4.29 ml, 17.2 mmol) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated to dryness and the remaining solid was triturated with heptane/EtOAc 2:1 for 4 h. Filtration delivered the title compound as white solid (217 mg, 74%). MS: 308.2 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe remaining solid was triturated with heptane/EtOAc 2:1 for 4 h
  3. filtrationFiltration

Sources & evidence

ORD record
ord-81d966bdfdbf4c14afcebef22788b0e2
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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