Hydrochloric Acid → HCID 53845575, compound

HRID 2398859Notes

Reaction equation

HRID 2398859 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:6][O:7][C:8]([NH:10][C@H:11]([C:20](OC)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:9].O.O.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>C(O)C.N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:6][O:7][C:8]([NH:10][C@H:11]([CH2:20][OH:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6093260Calcium chloride, dihydrateHCID 54225478HCID 54225478, compound

Product 1

HCID 53845575HCID 53845575, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

In a mixture of 80 ml of ethanol and 30 ml of pyridine, 6.54 g of methyl N-(3,4-dimethoxybenzyloxycarbonyl)-tyrosinate was dissolved. To the solution, 4.41 g of calcium chloride dihydrate was added. Then, to the mixture, 2.27 g of sodium borohydride was slowly added while stirring at room temperature. The resulting mixture was stirred for 3 hours and neutralized with 3% hydrochloric acid. After addition of 250 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 to give 3.82 g of N-(3,4-dimethoxy-benzyloxycarbonyl)-tyrosinol. The crystals were recrystallized from ethanol to give small needles with mp. 152°-155° C. Analysis, calculated for C19H23NO6 : C, 63.14; H, 6.42; N, 3.88; found C, 63.30; H, 6.29; N, 3.99.

Workup

  1. dissolutionwas dissolved
  2. stirringThe resulting mixture was stirred for 3 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1e5e88e046554bccabb6691a8f5fc5a0
Source dataset
uspto-grants-1977_05
Patent number
US04025644

Reaction notes

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