Hydrochloric Acid → HCID 54032578, compound

HRID 839932Notes

Reaction equation

HRID 839932 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+].B(F)(F)F.CCOCC.Cl>O1CCCC1>[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 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 54310629N-[(Cyclohexylmethoxy)carbonyl]-L-tyrosine

Product 1

HCID 54032578HCID 54032578, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of tetrahydrofuran was dissolved 1.0 g of N-(cyclohexylmethoxycarbonyl)-tyrosine. To the solution, 380 mg of sodium borohydride was added with stirring. After 10 minutes, to the mixture was added dropwise 15 ml of tetrahydrofuran solution containing 1.45 ml of boron trifluoride etherate. The mixture was stirred for 20 hours. After addition of 3% hydrochloric acid, the mixture was concentrated 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 N-(cyclohexylmethoxycarbonyl)tyrosinol.

Workup

  1. stirringThe mixture was stirred for 20 hours
  2. concentrationthe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. dissolutionThe residue was dissolved in chloroform

Sources & evidence

ORD record
ord-c7e71c5eee9b4b76b1a62bc71db7d724
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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