Hydrochloric Acid → HCID 14011739, compound

HRID 990027

Reaction equation

HRID 990027 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[C:21]([I:22])=[CH:20][C:13]([CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])=[CH:12][C:11]=2[I:23])=[CH:5][CH:4]=1.N[C@H:25](C(O)=O)CC1C=C(I)C(OC2C=C(I)C(O)=C(I)C=2)=C(I)C=1.C([O-])(O)=O.[Na+]>CO>[CH3:25][O:18][C:17](=[O:19])[C@H:15]([CH2:14][C:13]1[CH:12]=[C:11]([I:23])[C:10]([O:9][C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[C:21]([I:22])[CH:20]=1)[NH2:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5819ThyroxineHCID 928593,5-Diiodothyronine, L-HCID 516892Sodium Bicarbonate

Product 1

HCID 14011739HCID 14011739, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 6 M solution of HCl in MeOH (8 mL; 4.8 mmol) was added to a suspension of O-(4-hydroxyphenyl)3,5-diiodo-L-tyrosine (2.12 g; 5 mmol) (prepared according to: Chalmers J. R., Dickson G. T., Elks J. and Hems D. A., “The Synthesis of Thyroxine and Related Substances”, Part V., J. Chem. Soc. (1949), 3424-3433) in MeOH (12 was stirred for 4 days at 20° C. Then a NaHCO3 saturated aqueous solution was added to the mixture until pH 7 was reached, obtaining a precipitate which was filtered by concentration of the solution a second crop of precipitate was obtained. The two samples were combined and dried (50° C.; 1.3 kPa) 3.7 mmol). Yield 87%.

Workup

  1. customprepared
  2. customobtaining a precipitate which
  3. filtrationwas filtered by concentration of the solution a second crop of precipitate
  4. customwas obtained
  5. customdried (50° C.; 1.3 kPa) 3.7 mmol)

Sources & evidence

ORD record
ord-63772df48e1d40cdb38e7b6a1d3b5bff
Source dataset
uspto-grants-2002_10
Patent number
US06458337B1

Linked notes

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