Hydrochloric Acid → HCID 54191281, compound

HRID 279703Notes

Reaction equation

HRID 279703 reaction equation
C([O:3][C:4](=[O:19])[C@@H:5]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][N:6]1C(=O)C)C.Cl.O1CCOCC1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>CC(O)=O.[OH-].[Na+]>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([N:6]2[CH2:7][CH2:8][C@@H:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C@H:5]2[C:4]([OH:3])=[O:19])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 73974-Toluenesulfonyl chlorideHCID 312751,4-DioxaneHCID 18662956HCID 18662956, compound

Product 1

HCID 54191281HCID 54191281, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

N-Acetyl-cis-3-phenylproline ethyl ester (614 mg, 2.35 mmol) (prepared via the method of Chung, et al., J. Org. Chem.55: 270-275 (1990)) was dissolved in HOAc (4 mL) and 6N HCl (12 mL) and heated at reflux for 18 hr. The mixture was cooled to room temperature and the volatiles were evaporated in vacuo to give a white solid. The solid was dissolved in 1N NaOH (15 mL) and dioxane was added (10 mL), followed by 4-toluene-sulfonyl chloride (458 mg, 2.40 mmol). The mixture was stirred at room temp for 18 hr before addition of 6N HCl to bring the pH<4. The mixture was extracted with Et2O (3×40 mL) and the extracts were dried (MgSO4), filtered, and evaporated in vacuo to give N-(toluene-4-sulfonyl)-cis-3-phenylproline as a white solid (765 mg, 94%).

Workup

  1. temperatureat reflux for 18 hr
  2. customthe volatiles were evaporated in vacuo
  3. customto give a white solid
  4. extractionThe mixture was extracted with Et2O (3×40 mL)
  5. dry with materialthe extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-df86021289c84f62a89b2477a73719d6
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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