2-Iodobenzoic acid → HCID 68838718, compound

HRID 660577Notes

Reaction equation

HRID 660577 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[Si:33]([O:40][CH2:41][C@H:42]([NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[I:49])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>C1COCC1.C(N(CC)CC)C>[Si:33]([O:40][CH2:41][C@H:42]([NH:50][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[I:1])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[I:49])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 69412-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12178022HCID 12178022, compound

Product 1

HCID 68838718HCID 68838718, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-iodobenzoic acid (0.66 g, 2.65 mmol) in THF (90 mL) is added HOBt (0.71 g, 5.3 mmol). After the mixture is stirred at RT for 15 min, EDCl (1.0 g, 5.3 mmol) is added followed by triethylamine (1.1 mL). The mixture is stirred at RT for 20 min then (R)-2-(tert-butyldimethylsilanyloxy)-1-(2-iodophenyl)-ethylamine (Org. Lett. 6, 513 (2004)) (1.0 g, 2.65 mmol) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-60% EtOAc/hexane as eluent to give the title compound as a yellow solid.

Workup

  1. stirringThe mixture is stirred at RT for 20 min
  2. stirringstirring
  3. waitis continued for 18 h
  4. customThe solvent is removed under reduced pressure and water
  5. additionis added to the residue
  6. extractionThe mixture is extracted with EtOAc
  7. washthe organic phase is washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is removed under reduced pressure
  10. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-18b016ca5056481ab9a648be3ca213ba
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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