Hydrochloric Acid → HCID 22797793, compound

HRID 2398850Notes

Reaction equation

HRID 2398850 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][C:8]([NH:10][C@H:11]([C:20]([O-])=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:9])=[CH:4][CH:3]=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][C:8]([NH:10][C@H:11]([CH2:20][OH:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86734781HCID 86734781, compound

Product 1

HCID 22797793HCID 22797793, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 30 ml of tetrahydrofuran was dissolved 1.0 g of methyl (N-(4-chlorobenzyloxycarbonyl)-tyrosinate. To the solution was added dropwise 10 ml of tetrahydrofuran solution containing 4.2 ml of sodium dihydro-bis-(2-methoxyethoxy) aluminate (65% toluene solution) with stirring while cooling with ice. The mixture was stirred at room temperature for one hour. After addition of 200 ml of 3% hydrochloric acid, the reaction 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 509 mg of N-(4-chlorobenzyloxycarbonyl)-tyrosinol: yield 56%.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture was stirred at room temperature for one hour
  3. concentrationthe reaction 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-a3b4e52c6a774c168b1c6ecd7f95ad6e
Source dataset
uspto-grants-1977_05
Patent number
US04025644

Reaction notes

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