Ethanol → HCID 46889454, compound

HRID 926687Notes

Reaction equation

HRID 926687 reaction equation
[CH3:1][CH2:2]O.[CH3:4][CH2:5]OC(C)=O.CCO.CC(O)=O.O.[CH:18]1[C:23]([I:24])=[C:22]([O:25][C:26]2[CH:31]=[C:30]([I:32])[C:29]([OH:33])=[C:28]([I:34])[CH:27]=2)[C:21]([I:35])=[CH:20][C:19]=1[CH2:36][C@H:37]([NH2:41])[C:38]([OH:40])=[O:39]>O.CS(C)=O>[CH2:4]([O:39][C:38](=[O:40])[CH:37]([NH:41][CH2:1][CH3:2])[CH2:36][C:19]1[CH:20]=[C:21]([I:35])[C:22]([O:25][C:26]2[CH:27]=[C:28]([I:34])[C:29]([OH:33])=[C:30]([I:32])[CH:31]=2)=[C:23]([I:24])[CH:18]=1)[CH3:5]

Participants

7

Reactant 4

HCID 702EthanolHCID 5819ThyroxineHCID 21584252Ethanol ethylacetateHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 46889454HCID 46889454, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Yield: 50%; off-white solid; recrist. solvt.: EtOH; TLC: Rf=0.43 (EtOAc/EtOH 9/1); RPTLC: Rf=0.43 (AcOH/H2O 8/2); mp=136° C.; IR (υ cm−1): 1730 (CO); NMR (DMSO-d6) δ (ppm): 7.79 (s, 2H, ArH), 7.14 (s, 2H, ArH), 4.06-4.02 (m, 2H, CH2), 3.93-3.89 (q, J 7.0 Hz, 2H, CH2), 3.59-3.56 (t, J=7.0 Hz, 1H, CH), 2.80-2.77 (m, 2H, CH2), 1.88 (br, 1H, NH), 1.41-1.39 (t, J=7.0 Hz, 3H, CH3), 1.15-1.12 (t, J=7.0 Hz, 3H, CH3); MS (ESI+) m/z 911.7 [(M+DMSO)+, 100], 833.7 [(M+H)+, 75]; Anal. Calcd. for C19H19I4NO4: C, 27.40; H 2.30; N, 1.68. Found: C, 27.54; H, 1.94; N, 1.66. Solubility 10−3 M in water after preparing a solution at 10−1 M in DMSO. It is noteworthy that if a suspension of L-T4 is prepared overnight, the yield can be increased.

Workup

  1. customis prepared overnight
  2. customthe yield can
  3. temperaturebe increased

Sources & evidence

ORD record
ord-c41281ffdd1d474c891a14c719b181b5
Source dataset
uspto-grants-2016_03
Patent number
US09289395B2

Reaction notes

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