Hydrogen chloride-ethyl acetate → HCID 68415743, compound

HRID 1662078Notes

Reaction equation

HRID 1662078 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([O:36]C(C)(C)C)=[O:35])=[O:27])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:41].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:41].[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([OH:36])=[O:35])=[O:27])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86644638HCID 86644638, compound

Product 1

HCID 68415743HCID 68415743, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(3-methoxybenzyl)-L-ornithyl}amino)cyclopentanecarboxylate (0.28 g) and ethyl acetate (3.0 ml) was added a 4 M hydrogen chloride/ethyl acetate solution (3.0 ml) at room temperature, followed by stirring at room temperature over one night. The reaction mixture was concentrated under reduced pressure, and a saturated sodium bicarbonate solution was added to the residue for neutralization, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. To the compound obtained were added ethyl acetate and a 4 M-hydrogen chloride/ethyl acetate solution (0.5 mL), and the solid precipitated was collected by filtration to obtain (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(3-methoxybenzyl)-L-ornithyl}amino)cyclopentanecarboxylic acid hydrochloride (0.12 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated sodium bicarbonate solution was added to the residue for neutralization
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. customTo the compound obtained
  8. customa 4 M-hydrogen chloride/ethyl acetate solution (0.5 mL), and the solid precipitated
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8d1cb4a8cef248f0a70d3b2b2df86bea
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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