Sodium Carbonate → N-(2-methylbenzyloxycarbonyl)-tyrosinol

HRID 839936Notes

Reaction equation

HRID 839936 reaction equation
[NH2:1][C@H:2]([CH2:11][OH:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[CH2:16][O:17][C:18](Cl)=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[CH3:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[CH2:16][O:17][C:18]([NH:1][C@H:2]([CH2:11][OH:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 151247TyrosinolHCID 132929302-Methylbenzyloxycarbonyl chloride

Product 1

HCID 53904979N-(2-methylbenzyloxycarbonyl)-tyrosinolYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 10 ml of water and 20 ml of ethyl acetate, 1.6 g of tyrosinol was dissolved. To the solution were added dropwise 2 g of 2-methylbenzyloxycarbonyl choride and 10 ml of an aqueous solution containing 1.3 g of sodium carbonate alternately with stirring while cooling with ice. After stirring for two hours at room temperature, the ethyl acetate layer was collected and washed with 5% hydrochloric acid and then with water. The layer was dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum either to give 2.2 g of N-(2-methylbenzyloxycarbonyl)-tyrosinol with a mp. 78°-81° C in a yield of 70%. Analysis, calculated for C18H21O4N C 68.55, H 6.72, N 4.44, found C 68.88, H 6.84, N 4.42.

Workup

  1. dissolutionwas dissolved
  2. temperaturewhile cooling with ice
  3. stirringAfter stirring for two hours at room temperature
  4. customthe ethyl acetate layer was collected
  5. washwashed with 5% hydrochloric acid
  6. customThe layer was dried
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from ethyl acetate-petroleum

Sources & evidence

ORD record
ord-d3cef8fbe5ee4015892ec82d5269c328
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

Loading…