p-Toluenesulfonic acid monohydrate → HCID 68415245, compound

HRID 1662058Notes

Reaction equation

HRID 1662058 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][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[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][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[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 521998p-Toluenesulfonic acid monohydrateHCID 68411772HCID 68411772, compound

Product 1

HCID 68415245HCID 68415245, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-methoxybenzyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl}amino)cyclopentanecarboxylate (2.5 g) and methanol (25 ml) was added p-toluene sulfonic acid hydrate (1.2 g) at room temperature, followed by stirring at 40° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. Sodium hydrogen carbonate was added thereto under ice-cooling to adjust the pH to about 8, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (50 ml), and the organic layer was combined and extracted with a 10% aqueous citric acid solution. To the aqueous layer was added sodium hydrogen carbonate under ice-cooling to adjust the pH to about 8, followed by extraction with ethyl acetate and washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 4-methoxybenzyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (1.6 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the residue
  3. additionSodium hydrogen carbonate was added
  4. temperatureunder ice-cooling
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  7. extractionextracted with a 10% aqueous citric acid solution
  8. additionTo the aqueous layer was added sodium hydrogen carbonate under ice-
  9. temperaturecooling
  10. extractionfollowed by extraction with ethyl acetate
  11. washwashing with saturated brine
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f1091198fe84a8ebc7498b837681635
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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