Hydrogen Bromide → HCID 11688321, compound

HRID 2245347Notes

Reaction equation

HRID 2245347 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C@H:12]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])C1C=CC=CC=1.Br.CCOCC>C(O)(=O)C>[NH2:10][C@H:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C@H:12]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 68684634HCID 68684634, compound

Product 1

HCID 11688321HCID 11688321, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

(3R,4S)-[1-Phenethyl-3-(thiazolidine-3-carbonyl)-piperidine-4-yl]-carbamic acid benzyl ester (216 mg) was treated with 33% HBr in acetic acid (2.5 ml) for 2 hours at RT under argon. Ether (15 ml) was added and the resulting suspension was cooled to −10° C. and stirred for 1 hour. The solvent was then decanted and the solid washed with a small amount of EtOH. The residue was then dissolved in water (pH was adjusted to 10 with conc. NH4OH) and the aqueous layer was saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated to give a residue that was purified by flash chromatography (gradient of MeOH in DCM containing 0.5% NH4OH) to furnish the desired product as a light yellow oil (92 mg). MS (ESI): 320.1 MH+).

Workup

  1. customThe solvent was then decanted
  2. washthe solid washed with a small amount of EtOH
  3. dissolutionThe residue was then dissolved in water (pH was adjusted to 10 with conc. NH4OH)
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give a residue that
  10. customwas purified by flash chromatography (gradient of MeOH in DCM containing 0.5% NH4OH)

Sources & evidence

ORD record
ord-e70125707ff84fcdae12a1c3f16a4784
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

Loading…