Hydrochloric Acid → HCID 14011739, compound

HRID 1250127

Reaction equation

HRID 1250127 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×

Conditions

Temperature
20 °C

Procedure

A 6 M solution of HCl in MeOH (8 mL; 48 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., 3424-3433, 1949) in MeOH (12 mL). The resulting solution was left under stirring for 4 days at 20° C. Then an NaHCO3 aqueous saturated solution was added until pH 7, to obtain a precipitate which was filtered. After concentration of the solution, a second amount of precipitate was obtained. The two samples were combined and dried (50° C.; 1.3 kPa), to, give the desired product (2 g; 3.7 mmol). Yield 87%.

Workup

  1. customprepared
  2. waitThe resulting solution was left
  3. customto obtain a precipitate which
  4. filtrationwas filtered
  5. customAfter concentration of the solution, a second amount of precipitate was obtained
  6. customdried (50° C.; 1.3 kPa)

Sources & evidence

ORD record
ord-dbaea7d70c82471d8e3fd105c3f4713f
Source dataset
uspto-grants-2002_01
Patent number
US06337064B1

Linked notes

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