Pyridine → HCID 819487, compound

HRID 2284845Notes

Reaction equation

HRID 2284845 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.N1C=CC=CC=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([O-:19])=[O:18]>C(Cl)Cl.CCOC(C)=O>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([N:6]2[CH2:7][CH2:8][CH2:9][C@H:5]2[C:4]([O:3][CH3:2])=[O:10])(=[O:28])=[O:27])=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 819487HCID 819487, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-proline methyl ester hydrochloride salt (2.5 g, 15.2 mmol) in DCM (20 mL) was added pyridine (2.6 mL, 33 mmol) and 4-nitrobenzenesulfonyl chloride (3.06 g, 13.8 mmol) at 0° C. The resulting mixture was stirred at room temperature for 18 h and then diluted with EtOAc (100 mL). The organic phase was washed with 1 N HCl (20 mL), brine (20 mL) and dried over MgSO4. The mixture was filtered and the solvent was removed in vacuo to give a crude yellow solid that was used in the next step without further purification.

Workup

  1. washThe organic phase was washed with 1 N HCl (20 mL), brine (20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed in vacuo
  5. customto give a crude yellow solid that
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2f585d794a1943f286d44a1a6125eb70
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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