Hydrochloric Acid → HCID 15432053, compound

HRID 726452Notes

Reaction equation

HRID 726452 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 2N sodium hydroxide. Cyclohexanoyl chloride (49.32 mL, 0.34 mole) was added dropwise to the mixture. Additional aqueous 2N 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 2N 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 2N sodium hydroxide
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-28c9de2bdbf445199c581866de71d97e
Source dataset
uspto-grants-1998_01
Patent number
US05709861

Reaction notes

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