Hydrochloric Acid → HCID 89824995, compound

HRID 2277098Notes

Reaction equation

HRID 2277098 reaction equation
C([O-])([O-])=O.[K+].[K+].C([O:10][C@H:11]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][C@H:15]1[C:20](=[O:39])[NH:21][CH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:13])(=O)C.Cl>CO.CCOC(C)=O>[Cl:29][C:27]1[CH:26]=[CH:25][C:24]([CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[C:23]([CH2:22][NH:21][C:20]([C@@H:15]2[CH2:16][O:17][CH2:18][CH2:19][N:14]2[C:12](=[O:13])[C@H:11]([OH:10])[C:40]([CH3:43])([CH3:42])[CH3:41])=[O:39])[CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89824921HCID 89824921, compound

Product 1

HCID 89824995HCID 89824995, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (0.016 g, 0.11 mmol) was added to a solution of (R)-1-{(S)-3-[2-{(tert-Butoxycarbonylamino)methyl}-5-chlorobenzylcarbamoyl]morpholino}-3,3-dimethyl-1-oxo-butan-2-yl acetate (0.28 g, 0.51 mmol) in MeOH (3 mL) and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc (20 mL), acidified with 1N aqueous HCl (5 mL) and the extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine solution (10 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel; eluent: 70% EtOAc/hexanes) to afford the title compound as a pale yellow oil (0.25 g).

Workup

  1. extractionthe extracted with EtOAc (2×20 mL)
  2. washThe combined organic layers were washed with brine solution (10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel; eluent: 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7168f60276c040e28c8014a17812079e
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

Loading…