Sodium Bicarbonate → HCID 86720279, compound

HRID 1754319Notes

Reaction equation

HRID 1754319 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].C(=O)(O)[O-].[Na+].[NH:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([O:25]C(C)(C)C)=[O:24]>C(Cl)Cl>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23]([OH:25])=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27592104-Formylbenzene-1-sulfonyl chlorideHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 86720279HCID 86720279, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution of 4-formylbenzenesulfonyl chloride (1 g, 5 mmol) in DCM (10 mL), was added saturated aqueous sodium bicarbonate solution (10 mL), followed by tert-butyl(2S)-pyrrolidine-2-carboxylate (856 mg, 5 mmol). The organic phase was passed through a hydrophobic frit, and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 0-100% EtOAc in isohexane, to afford the title compound as a colourless gum (849 mg, 60%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude material was purified by silica gel column chromatography
  3. washeluting with 0-100% EtOAc in isohexane

Sources & evidence

ORD record
ord-d556b067f0a3405e8e35d2459d8ea0f7
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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