Triethylamine → HCID 54032578, compound

HRID 839929Notes

Reaction equation

HRID 839929 reaction equation
[CH:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:21](O)=[O:22])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)OCC.C(N(CC)CC)C>O1CCCC1>[CH:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([CH2:21][OH:22])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 54310629N-[(Cyclohexylmethoxy)carbonyl]-L-tyrosine

Product 1

HCID 54032578HCID 54032578, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran, 3.2 g of N-(cyclohexylmethoxycarbonyl)-tyrosine was dissolved. To the solution were added 1.1 g of ethyl chlorocarbonate and 1.0 g of triethylamine while cooling with ice and stirring. After stirring the mixture for 10 minutes, the precipitate was removed by filtration. The filtrate was added to a suspension of 1.0 g of sodium borohydride and 10 ml of tetrahydrofuran cooled with ice. The mixture was stirred for two hours, then neutralized with hydrochloric acid and concentrated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethylacetate-petroleum ether to give 2.3 g of N-(cyclohexylmethoxycarbonyl)-tyrosinol with a melting point of 121° - 126° C.

Workup

  1. temperaturewhile cooling with ice
  2. stirringAfter stirring the mixture for 10 minutes
  3. customthe precipitate was removed by filtration
  4. additionThe filtrate was added to a suspension of 1.0 g of sodium borohydride and 10 ml of tetrahydrofuran
  5. temperaturecooled with ice
  6. stirringThe mixture was stirred for two hours
  7. concentrationconcentrated in vacuo
  8. extractionThe residue was extracted with ethyl acetate
  9. washthe extract was washed with water
  10. customdried
  11. concentrationconcentrated to dryness
  12. customThe residue was crystallized from ethylacetate-petroleum ether

Sources & evidence

ORD record
ord-44240f59cca94041bec243954499b481
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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