Hydrochloric Acid → HCID 118194683, compound

HRID 1770380Notes

Reaction equation

HRID 1770380 reaction equation
[CH2:1]([C@H:6]1[C@H:14]([CH3:15])[O:13][C:12](=[O:16])[C@@H:11]([NH:17]C(=O)OC(C)(C)C)[CH2:10][CH2:9][CH2:8][C@@H:7]1[O:25][CH2:26][CH2:27][CH3:28])[CH2:2][CH:3]([CH3:5])[CH3:4].[ClH:29].O1CCOCC1>C(Cl)Cl>[Cl-:29].[CH2:1]([C@H:6]1[C@H:14]([CH3:15])[O:13][C:12](=[O:16])[C@@H:11]([NH3+:17])[CH2:10][CH2:9][CH2:8][C@@H:7]1[O:25][CH2:26][CH2:27][CH3:28])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118199349HCID 118199349, compound

Product 1

HCID 118194683HCID 118194683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)carbamate (330 mg, 0.826 mmol) in DCM (3 mL) was added a solution of HCl in dioxane (2.07 mL, 8.26 mmol, 4M) under N2 and the resulting solution was stirred at room temperature for 2 h. The solvent was removed under a stream of N2, which afforded a white solid. This solid was triturated with Et2O (3×3 mL) and the resulting powder was dried under high vacuum for 1 h to give (3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-aminium chloride (59): ESIMS m/z 300 ([M+H]+).

Workup

  1. customThe solvent was removed under a stream of N2, which
  2. customafforded a white solid
  3. customThis solid was triturated with Et2O (3×3 mL)
  4. customthe resulting powder was dried under high vacuum for 1 h

Sources & evidence

ORD record
ord-3325952086a340d2b3fce59dcd131fb9
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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