Thyroxine → HCID 88038564, compound

HRID 1168899Notes

Reaction equation

HRID 1168899 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.C(N(CC)CC)C.[CH3:32][Si:33]([CH3:48])([CH3:47])[CH2:34][CH2:35][O:36][C:37](ON1C(=O)CCC1=O)=[O:38].S([O-])(O)(=O)=O.[K+]>CS(C)=O.O>[CH3:32][Si:33]([CH2:34][CH2:35][O:36][C:37]([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:38])([CH3:48])[CH3:47]

Participants

7

Reactant 4

HCID 5819ThyroxineHCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 88038564HCID 88038564, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of thyroxine (1.66 g, 2.14 mmol) in DMSO (15 mL) was added triethylamine (3.21 mmol) followed by solid Teoc-0Su (610 mg, 2.35 mmol). The mixture was stirred at room temperature overnight then diluted with water (22 mL), acidified with saturated potassium hydrogen sulfate solution and extracted with ether (3×45 mL). The combined organic extracts were washed with water (4×45 mL), dried with magnesium sulfate, and evaporated to dryness. (Yield: 1.87 g).

Workup

  1. extractionextracted with ether (3×45 mL)
  2. washThe combined organic extracts were washed with water (4×45 mL)
  3. dry with materialdried with magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-853cf653229c4f04bebd2e7176412045
Source dataset
uspto-grants-2003_09
Patent number
US06627660B1

Reaction notes

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