Hydrochloric Acid → HCID 54032578, compound

HRID 1438995Notes

Reaction equation

HRID 1438995 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:13][O:14][C:15]([NH:17][C@H:18]([C:27](O)=[O:28])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>O1CCCC1>[CH:7]1([CH2:13][O:14][C:15]([NH:17][C@H:18]([CH2:27][OH:28])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 54310629N-[(Cyclohexylmethoxy)carbonyl]-L-tyrosine

Product 1

HCID 54032578HCID 54032578, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of tetrahydrofuran, 574 mg of lithium aluminum hydride was suspended. To the suspension was added dropwise 20 ml of tetrahydrafuran solution containing 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. additionTo the suspension was added dropwise 20 ml of tetrahydrafuran solution
  2. temperaturecooling with ice
  3. stirringThe mixture was stirred at room temperature for two hours
  4. concentrationthe mixture was concentrated in vacuo
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. dissolutionThe residue was dissolved in chloroform

Sources & evidence

ORD record
ord-0e9864b2954a44439a29fa28c894ea6f
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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