Sodium Carbonate → HCID 22324511, compound

HRID 1582413Notes

Reaction equation

HRID 1582413 reaction equation
[CH2:1]1[C@@H:4]([C:5]([OH:7])=[O:6])[NH:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]([S:22](Cl)(=[O:24])=[O:23])[CH:18]=[C:19]([Cl:21])[CH:20]=1>O.CCOCC>[Cl:21][C:19]1[CH:18]=[C:17]([S:22]([N:3]2[CH2:2][CH2:1][CH:4]2[C:5]([OH:7])=[O:6])(=[O:23])=[O:24])[CH:16]=[C:15]([Cl:14])[CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 164862-Azetidinecarboxylic acid, (S)-HCID 5223883,5-Dichlorobenzenesulfonyl chloride

Product 1

HCID 22324511HCID 22324511, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.0 g (19.8 mmol) of (L)-azetidine-2-carboxylic acid and 4.6 g (43.6 mmol) of Na2CO3 in 100 mL of H2O at 0° C. was added 5.8 g (23.8 mmol) of 3,5-dichlorophenylsulfonylchloride. The reaction was allowed to come to room temperature overnight and was then diluted with Et2O and H2O. The layers were separated and the organic phase was discarded. The aqueous phase was acidified to pH˜4 with 1M HCl and extracted with EtOAc (4×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated to give N-(3,5-dichlorophenylsulfonyl)-azetidine-2-carboxylic acid (6.0 g, 100%) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionextracted with EtOAc (4×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48e957f04b0f4134bd3c9a712b0e195c
Source dataset
uspto-grants-2004_05
Patent number
US06734311B2

Reaction notes

Loading…