Hydrochloric Acid → (1R,3S,5S)-5-Hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide hydrochloride

HRID 1527433Notes

Reaction equation

HRID 1527433 reaction equation
C(OC([N:8]1[C@H:13]([C:14](=[O:28])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[C:17]=2[F:27])[CH2:12][C@:11]2([CH2:29][O:30]C3CCCCO3)[C@H:9]1[CH2:10]2)=O)(C)(C)C.[ClH:37]>O1CCOCC1>[ClH:37].[F:27][C:17]1[C:18]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:14]([C@@H:13]1[CH2:12][C@:11]2([CH2:29][OH:30])[C@@H:9]([CH2:10]2)[NH:8]1)=[O:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68283049(1R,3S,5S)-3-(2-Fluoro-3-trifluoromethoxy-phenylcarbamoyl)-5-(tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Product 1

HCID 86673857(1R,3S,5S)-5-Hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoromethoxy-phenyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (1R,3S,5S)-3-(2-fluoro-3-trifluoromethoxy-phenylcarbamoyl)-5-(tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (105 mg, 0.19 mmol) in dioxane (0.5 mL) was added HCl (4 N in dioxane, 481 μL, 1.92 mmol). The mixture was stirred at RT for 4 h, solvent was removed under reduced pressure and the material thus obtained was used without further purification in the next step. MS (UPLC/MS): 335.2 [M+H]+, 333.2 [M−H]−, 379.6 [M+HCOO]−.

Workup

  1. customsolvent was removed under reduced pressure
  2. customthe material thus obtained
  3. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-2fa5e2217591437bbe632e282326f240
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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