Hydrochloric Acid → HCID 70544140, compound

HRID 1759380Notes

Reaction equation

HRID 1759380 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].[NH2:10][C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(OCC)C.C(Cl)(Cl)Cl>[C:1]([NH:10][C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:31]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:32])=[CH:17][CH:18]=1)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6057L-TyrosineHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide4×HCID 61186Valeryl chloride

Product 1

HCID 70544140HCID 70544140, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A solution of 6.0 g (50 m-mol) of pentanoyl chloride in ethyl ether (50 ml) and an aqueous solution (26 ml) of 2N-sodium hydroxide were added dropwise at the same time over the period of 30 minutes to an aqueous 2N-sodium hydroxide solution (38.5 ml) of 7.00 g (38.6 m-mol) of tyrosine under agitation at 5° C., while maintaining the pH value between 9 and 11. The mixture was stirred for an additional 2 hours at room temperature and, after addition of 2N-sodium hydroxide (5 ml) thereto, was warmed at 70° C. for 10 minutes. After cooling the reaction liquid at -10° C., 9.87 g (58m-mol) of benzyloxycarbonyl chloride and an aqueous 2N-sodium hydroxide solution (20.5 ml) were added dropwise at the same time to the reaction liquid under vigorous agitation. After completion of the reaction, 3N-hydrochloric acid was added to the reaction mixture to adjust the pH value to 3. A white precipitate formed was collected by filtration and recrystallized from chloroform whereby 12.80 g (yield: 82.9%) of N-pentanoyl-O-benzyloxycarbonyltyrosin was obtained.

Workup

  1. temperaturewhile maintaining the pH value between 9 and 11
  2. temperaturewas warmed at 70° C. for 10 minutes
  3. temperatureAfter cooling
  4. customthe reaction liquid at -10° C.
  5. additionwas added to the reaction mixture
  6. customA white precipitate formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f520804c9846430e98ea3958d445789d
Source dataset
uspto-grants-1982_07
Patent number
US04340728

Reaction notes

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