Hydrochloric Acid → HCID 54032578, compound

HRID 2398845Notes

Reaction equation

HRID 2398845 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.Cl>O1CCCC1.C1(C)C=CC=CC=1>[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 2

HCID 313Hydrochloric AcidHCID 54310629N-[(Cyclohexylmethoxy)carbonyl]-L-tyrosine

Product 1

HCID 54032578HCID 54032578, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 20 ml of tetrahydrofuran was dissolved 10 ml of a 65% toluene solution of sodium dihydrobis-(2-methoxyethoxy)-aluminate. To the solution was added dropwise 20 ml of tetrahydrofuran solution and 1.0 g of N-(cyclohexylmethoxycarbonyl)-tyrosine while stirring and cooling with ice. The mixture was stirred at room temperature for two hours. After addition of 5% hydrochloric acid, the mixture was concentrated in vacuo and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was dissolved in chloroform and subjected to column chromatography with 10 g of silicagel to give 322 mg of N-(cyclohexylmethoxycarbonyl)-tyrosinol.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture was stirred at room temperature for two hours
  3. concentrationthe mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue was dissolved in chloroform

Sources & evidence

ORD record
ord-aaeb831999ac4e8cbfa10c3de4f3a514
Source dataset
uspto-grants-1977_05
Patent number
US04025644

Reaction notes

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