Hydrochloric Acid → HCID 54032578, compound

HRID 1438996Notes

Reaction equation

HRID 1438996 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 42.9%

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 2 hours. After addition of 5% hydrochloric acid, the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was crystallized from ethyl acetate-petroleum ether to give 410 mg of N-(cyclohexylmethoxycarbonyl)-tyrosinol.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-a379986d3e8c40669a58befa8d7fbb05
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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