Sodium Carbonate → HCID 12068278, compound

HRID 1058201Notes

Reaction equation

HRID 1058201 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chlorideHCID 145742L-Proline

Product 1

HCID 12068278HCID 12068278, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitrobenzenesulfonyl chloride (5.79 g) was added to a mixed solution of tetrahydrofuran (20 ml)/water (17 ml) containing (S)-proline (2.00 g), 5 N sodium hydroxide (3.5 ml) and sodium carbonate (3.77 g) under ice cooling, followed by stirring for 1 hour under ice cooling and for 22 hours at room temperature. Water (20 ml) was added to the reaction mixture, and the organic solvent was removed by evaporation under reduced pressure. Then, water (20 ml), 5 N sodium hydroxide (4 ml) and ethyl acetate (100 ml) were added, followed by extraction and solution separation, and the organic layer was extracted again with water (15 ml). Ethyl acetate (50 ml) and 6 N hydrochloric acid (20 ml) were added to the resulting aqueous layer, followed by extraction and solution separation, and the aqueous layer was extracted again with ethyl acetate (50 ml). The resulting organic layer was dried over sodium sulfate, filtered, concentrated and dried under vacuum to obtain (S)-N-(2-nitrobenzenesulfonyl)proline (5.53 g; yield: quantitative).

Workup

  1. customthe organic solvent was removed by evaporation under reduced pressure
  2. additionThen, water (20 ml), 5 N sodium hydroxide (4 ml) and ethyl acetate (100 ml) were added
  3. extractionfollowed by extraction and solution separation
  4. extractionthe organic layer was extracted again with water (15 ml)
  5. additionEthyl acetate (50 ml) and 6 N hydrochloric acid (20 ml) were added to the resulting aqueous layer
  6. extractionfollowed by extraction and solution separation
  7. extractionthe aqueous layer was extracted again with ethyl acetate (50 ml)
  8. dry with materialThe resulting organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-94496590f11e4b2887f945d07c3a2caa
Source dataset
uspto-grants-2003_02
Patent number
US06515179B2

Reaction notes

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