Hydrochloric Acid → HCID 22867972, compound

HRID 482131Notes

Reaction equation

HRID 482131 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].O1CCCC1.Cl>[OH-].[Na+]>[CH3:13][S:14]([NH:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chloride

Product 1

HCID 22867972HCID 22867972, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of L-phenylalanine 1.65 g (10 mmol) in 2N sodium hydroxide aqueous solution, cooled in an ice-water bath and under vigorous stirring, a mixture of methanesulfonyl chloride 1.26 g (11 mmol) and tetrahydrofuran 3 ml, and 2N sodium hydroxide aqueous solution 6 ml were added dropwise and alternately each in three portions. After completion of addition stirring was continued under ice-water cooling for 5 minutes, further, at room temperature for 1 hour. 6N hydrochloric acid 2 ml was added, and extraction was made with 30 ml of chloroform. Organic layer was washed with water and dried, and the solvent distilled off to obtain crude N-Ms-L-Phe as an oil. The crude product was purified by silica gel column chromatography- (eluent: chloroform, ethyl acetate) to give pure N-Ms-L-Phe 1.00 g as an oil. The yield based on the used L-phenylalanine was 41.0%.

Workup

  1. additionwere added dropwise
  2. additionAfter completion of addition
  3. waitfurther, at room temperature for 1 hour
  4. extractionextraction
  5. washOrganic layer was washed with water
  6. customdried
  7. distillationthe solvent distilled off
  8. customto obtain crude N-Ms-L-Phe as an oil
  9. customThe crude product was purified by silica gel column chromatography- (eluent: chloroform, ethyl acetate)

Sources & evidence

ORD record
ord-b3c19e0bfaa04d2d93361487b8c9907e
Source dataset
uspto-grants-1998_08
Patent number
US05792869

Reaction notes

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