Sodium Chloride → N-Trifluoroacetylthyroxine

HRID 1732551Notes

Reaction equation

HRID 1732551 reaction equation
[NH2:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][C:4]1[CH:11]=[C:9]([I:10])[C:8]([O:12][C:13]2[CH:20]=[C:18]([I:19])[C:17]([OH:21])=[C:15]([I:16])[CH:14]=2)=[C:6]([I:7])[CH:5]=1.[F:25][C:26]([F:31])([F:30])[C:27](O)=[O:28].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl-].[Na+]>C(OCC)(=O)C.O>[F:25][C:26]([F:31])([F:30])[C:27]([NH:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][C:4]1[CH:5]=[C:6]([I:7])[C:8]([O:12][C:13]2[CH:14]=[C:15]([I:16])[C:17]([OH:21])=[C:18]([I:19])[CH:20]=2)=[C:9]([I:10])[CH:11]=1)=[O:28]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 5819ThyroxineHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydride

Product 1

HCID 12831641N-Trifluoroacetylthyroxine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 20 g [25.6 millimoles (mmol)] of L-thyroxine (Sigma Chemical Co., St. Louis, Missouri USA) in 240 ml of dry ethyl acetate containing 46 ml of trifluoroacetic acid and 7.6 ml of trifluoroacetic anhydride was stirred at 0° C. for one hour. Upon warming to room temperature and adding 200 ml of H2O, a suspension formed which was then saturated with sodium chloride. The organic phase of the mixture was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to give 21.3 g of the N-protected thyroxine derivative (6). A sample was recrystallized from ether-pentane to give fine crystals, m.p. 233°-235° C. (decomposed).

Workup

  1. customa suspension formed which
  2. customThe organic phase of the mixture was separated
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1e1e0100439043f4b027b084bc7361ed
Source dataset
uspto-grants-1980_12
Patent number
US04238395

Reaction notes

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