Hydrochloric Acid → HCID 7201379, compound

HRID 1645970Notes

Reaction equation

HRID 1645970 reaction equation
[OH-].[Na+].[NH:3]1[CH2:10][CH2:9][CH2:8][C@H:4]1[C:5]([OH:7])=[O:6].[N+:11]([C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].Cl>O.C(OCC)C>[N+:11]([C:14]1[CH:15]=[C:16]([S:20]([N:3]2[CH2:10][CH2:9][CH2:8][C@H:4]2[C:5]([OH:7])=[O:6])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 84763-Nitrobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 145742L-Proline

Product 1

HCID 7201379HCID 7201379, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
15 °C

Procedure

To solution of 12.0 g of sodium hydroxide in 150 ml of water was added 15.0 g of L-proline and dissolved under water-cooling at 15° C. The solution was stirred under water-cooling at 15° C. and to the reaction mixture was added 30.0 g of 3-nitrobenzenesulfonyl chloride and 15 ml of diethyl ether under stirring for 15 minutes. After stirring at room temperature for 80 minutes, the reaction mixture was acidified at pH2 with concentrated hydrochloric acid and the separated oily substance was extracted with ethyl acetate. After the organic layer was washed with aqueous sodium chloride, the solution was filtered and the filtrate was concentrated under reduced pressure. The crystallized residue was boiled with 300 ml of hexane-ethyl acetate (1:1) and was cooled. The obtained crystals were collected by filtration to give 31.7 g of N-3-nitrobenzenesulfonyl-L-proline, melting at 155°-157° C., [α]23D =-71.3° (c=1, CHCl3)

Workup

  1. dissolutiondissolved under water-
  2. temperaturecooling at 15° C. and to the reaction mixture
  3. stirringunder stirring for 15 minutes
  4. stirringAfter stirring at room temperature for 80 minutes
  5. extractionthe separated oily substance was extracted with ethyl acetate
  6. washAfter the organic layer was washed with aqueous sodium chloride
  7. filtrationthe solution was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. temperaturewas cooled
  10. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-f893430814ca4646ba68e1f8e5b0a50e
Source dataset
uspto-grants-1993_01
Patent number
US05177216

Reaction notes

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