Hydrochloric Acid → HCID 68415751, compound

HRID 1662076Notes

Reaction equation

HRID 1662076 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[C:8]([NH:10][C@H:11]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([O:36]C)=[O:35])=[O:27])[CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:9])(=O)C.CO.[OH-].[Na+].Cl>C1COCC1>[CH2:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][CH2:12][C@@H:11]([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:10][C:8](=[O:9])[C:7]1[CH:38]=[CH:39][CH:40]=[C:5]([OH:4])[CH:6]=1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 86644635HCID 86644635, compound

Product 1

HCID 68415751HCID 68415751, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl (1R,2S)-2-({N2-(3-acetoxybenzoyl)-N5-[(benzyloxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.35 g), methanol (3.0 ml), and THF (3.0 ml) was added a 1 M aqueous sodium hydroxide solution (1.9 ml) under ice-cooling, followed by stirring at room temperature over one night. Further, to the reaction mixture were added a 1 M aqueous sodium hydroxide solution (1.0 ml) under ice-cooling, followed by stirring at room temperature for 4 hours. After completion of the reaction, 1 M hydrochloric acid was added thereto under ice-cooling, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and diisopropyl ether and ethyl acetate were added to the purified product obtained to give a solid. The solid was collected by filtration to obtain (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(3-hydroxybenzoyl)-L-ornithyl}amino)cyclopentanecarboxylic acid (0.12 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 4 hours
  4. additionwas added
  5. temperatureunder ice-cooling
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography, and diisopropyl ether and ethyl acetate
  10. additionwere added to the purified product
  11. customobtained
  12. customto give a solid
  13. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-6b57411ad3944071bdee944f65acf3d9
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

Loading…