Hydrogen chloride-ethyl acetate → HCID 86761425, compound

HRID 1662043Notes

Reaction equation

HRID 1662043 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:24]([NH:26][C@H:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C:32]([O:34][CH3:35])=[O:33])=[O:25])[NH:16]C(OC(C)(C)C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:24]([NH:26][C@H:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C:32]([O:34][CH3:35])=[O:33])=[O:25])[NH2:16])=[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 86761426HCID 86761426, compound

Product 1

HCID 86761425HCID 86761425, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl}amino)cyclopentanecarboxylate (11.33 g) was suspended in ethyl acetate (34 ml), and a 4 M hydrogen chloride/ethyl acetate solution (52 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added ethyl acetate (150 ml) and a saturated sodium bicarbonate solution (150 ml), followed by stirring for 5 minutes and performing a liquid separation operation. The aqueous layer was extracted with ethyl acetate (100 ml), and then the organic layer was combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to obtain methyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (9.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue were added ethyl acetate (150 ml)
  3. stirringby stirring for 5 minutes
  4. customa liquid separation operation
  5. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-11e232f64e0d438b8f3887a6c67b4675
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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