Hydrochloric Acid → HCID 15432053, compound

HRID 397246Notes

Reaction equation

HRID 397246 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>[OH-].[Na+]>[CH:14]1([C:20]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:10][C:20]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:21])=[CH:8][CH:9]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6057L-TyrosineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 15432053HCID 15432053, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

(L)-Tyrosine (61.6 g., 0.34 mole) was dissolved in 190 mL of 2 N sodium hydroxide. Cyclohexanoyl chloride (49.32 mL, 0.34 mole) was added dropwise to the mixture. Additional aqueous 2 N sodium hydroxide was added, and the reaction mixture was allowed to stir at room temperature for 2 hours. The mixture was then acidified to pH 9.5 with aqueous (4:1) hydrochloric acid. A precipitate formed which was separated by vacuum filtration. The solids were dissolved in 2 N sodium hydroxide and dried by lyophilization to furnish 33.5 g of N,O-dicyclohexanoyl-(L)-tyrosine. The product was purified by column chromatography on silica gel using butanol/acetic acid/water as the eluent system. The pure product was a white solid.

Workup

  1. customA precipitate formed which
  2. customwas separated by vacuum filtration
  3. dissolutionThe solids were dissolved in 2 N sodium hydroxide
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-cb0e6a285713449bbc427f204297926d
Source dataset
uspto-grants-2003_08
Patent number
US06610329B2

Reaction notes

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