Hydrochloric Acid → HCID 53845575, compound

HRID 839944Notes

Reaction equation

HRID 839944 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 three 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-dimethoxybenzyloxycarbonyl)-tyrosinol. The crystals were recrystallized from ethanol to give small needles with mp. 152°-155° C. Analysis, calculated for C19H23 NO6C 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 three 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-5a9518d4644a4433ad73151fba5829ab
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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