Anisole → HCID 66672433, compound

HRID 1622042Notes

Reaction equation

HRID 1622042 reaction equation
C1(OC)C=CC=CC=1.COC1C=CC(C[O:16][C:17](=[O:64])[CH:18]([NH:33][C:34]([NH:36][CH:37]([C:52]([O:54]CC2C=CC(OC)=CC=2)=[O:53])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43](=[O:51])[C:44]2[CH:49]=[CH:48][C:47]([I:50])=[CH:46][CH:45]=2)=[O:35])[CH2:19][CH2:20][C:21]([O:23]CC2C=CC(OC)=CC=2)=[O:22])=CC=1>C(O)(C(F)(F)F)=O>[C:52]([CH:37]([NH:36][C:34](=[O:35])[NH:33][CH:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:17]([OH:64])=[O:16])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43](=[O:51])[C:44]1[CH:45]=[CH:46][C:47]([I:50])=[CH:48][CH:49]=1)([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 74399626HCID 74399626, compound

Product 1

HCID 66672433HCID 66672433, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3% anisole in TFA (15 mL) was added to 2 (0.117 g, 0.129 mmol) at 0° C. The mixture was stirred at room temperature for 30 min then concentrated on a rotary evaporator. The crude material was purified by HPLC (Econosil C18 10μ, 250×10 mm, H2O/CH3CN/TFA (70/30/0.1), 4 mL/min, 3 eluting at 11 min) to afford 0.040 g (57%) of 3. 1H NMR (400 MHz, D2O:CD3CN=1:1 (v/v)) δ 7.79 (d, J=8.0 Hz, 2H), 7.46 (d, J=8.0 Hz, 2H), 4.08-4.16 (m, 2H), 3.26 (m, 2H), 2.35 (m, 2H), 2.00-2.03 (m, 1H), 1.72-1.84 (m, 2H), 1.52-1.62 (m, 3H), 1.34-1.36 (m, 2H). ESI-Mass calcd for C19H24IN3O8Na [M+Na]+ 572.1. found 572.0. FAB-HRMS calcd for C19H25IN3O8 [M+H]+ 550.0686. found 550.0648.

Workup

  1. concentrationthen concentrated on a rotary evaporator
  2. customThe crude material was purified by HPLC (Econosil C18 10μ, 250×10 mm, H2O/CH3CN/TFA (70/30/0.1), 4 mL/min, 3 eluting at 11 min)

Sources & evidence

ORD record
ord-bf64bc653a9347fd82fbca088b06c46b
Source dataset
uspto-grants-2014_07
Patent number
US08778305B2

Reaction notes

Loading…