Water → HCID 54032578, compound

HRID 2398848Notes

Reaction equation

HRID 2398848 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.[BH4-].[Na+].[Al].O>COCCOCCOC>[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

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5359268AluminumHCID 54310629N-[(Cyclohexylmethoxy)carbonyl]-L-tyrosine

Product 1

HCID 54032578HCID 54032578, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

In 15 ml of diglyme (bis (2-methoxyethyl) ether) was dissolved 1.0 g of N-(cyclohexylmethoxycarbonyl)-tyrosine. To the solution were added 570 mg of sodium borohydride and 50 ml of diglyme solution containing 7g of anhydrous aluminium chyloride. The mixture was stirred at room temperature for two hours. After addition of 150 ml of water, the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum ether to give N-(cyclohexylmethoxycarbonyl)-tyrosinol.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-46ef1fe0a98d4b7c80bbc65cf684fbb3
Source dataset
uspto-grants-1977_05
Patent number
US04025644

Reaction notes

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