Hydrochloric Acid → HCID 54242019, compound

HRID 1439009Notes

Reaction equation

HRID 1439009 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].[OH2:29].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])[C: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])=[O:29]

Participants

8

Reactant 4

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

Product 1

HCID 54242019HCID 54242019, compoundYield 60.6%

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-dimethoxybenzoyloxycarbonyl)-tyrosinol. The crystals were recrystallized from ethanol to give small needles with mp. 152°-155° C. Analysis, calculated for C19H23NO6C 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-63e3e366bcb54b7581a55c978c9a2e19
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

Loading…