Hydrochloric Acid → Hydrochloric Acid

HRID 1850228Notes

Reaction equation

HRID 1850228 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1.[ClH:28].O1CCOCC1>CO>[NH2:20][C@H:18]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)=[O:17])=[C:2]([F:1])[CH:3]=1)[CH3:19].[ClH:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178462190HCID 178462190, compound

Product 2

HCID 313Hydrochloric AcidHCID 178461844HCID 178461844, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl (S)-1-(3-fluoro-4-(trans-4-hydroxycyclohexylcarbamoyl)phenyl)ethylcarbamate (33 mg, 0.087 mmol) was added, HCl 4M in Dioxane (2 mL, 8.00 mmol) and MeOH (0.2 ml). The reaction was stirred at room temperature for 1 hour, followed by LCMS. The solvent was concentrated off to residue to give 4-((S)-1-aminoethyl)-2-fluoro-N-(trans-4-hydroxycyclohexyl)benzamide in quantitative yield (0.087 mmol) as HCl salt. LCMS m/z 281.1 (M+H)+, Rt 0.33 min.

Workup

  1. concentrationThe solvent was concentrated off to residue

Sources & evidence

ORD record
ord-d1a80e693b4e4d3988a0996bacf96054
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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