Hydrochloric Acid → HCID 22797793, compound

HRID 1439000Notes

Reaction equation

HRID 1439000 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]([NH:10][C@H:11]([C:20](OC)=[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.[H-].[Al+3].[Na+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:25]=[CH:24][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21862873HCID 21862873, compoundHCID 53762049HCID 53762049, compound

Product 1

HCID 22797793HCID 22797793, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran was dissoled 1.0 g of methyl N-(4-chlorobenzyloxycarbonyl)tyrosinate. To the solution was slowly added 280 mg of sodium aluminium hydride with stirring and the mixture was stirred for two hours. After addition of 50 ml of 1N hydrochloric acid, the mixture was 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 ethyl acetate-petroleum ether to give 610 mg of N-(4-chlorobenzyloxycarbonyl)-tyrosinol: yield 66%.

Workup

  1. stirringthe mixture was stirred for two hours
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-ea9c502beda146738e1f83ea8ea3833a
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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