Iodine → HCID 10013959, compound

HRID 601629Notes

Reaction equation

HRID 601629 reaction equation
II.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:29]([O:33][C:34](=[O:45])[NH:35][CH2:36][CH2:37][C:38]([NH:40][NH:41][C:42](=[O:44])[CH3:43])=O)([CH3:32])([CH3:31])[CH3:30]>C(Cl)Cl>[C:29]([O:33][C:34](=[O:45])[NH:35][CH2:36][CH2:37][C:38]1[O:44][C:42]([CH3:43])=[N:41][N:40]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 9992082HCID 9992082, compound

Product 1

HCID 10013959HCID 10013959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (0.261 g, 1.028 mmol) is added to a stirred solution of polymer supported triphenylphosphine (3 mmol/g, 0.34 g, 1.03 mmol) in DCM (10 ml). After stirring for 10 min at room temperature triethylamine (0.287 ml, 2.06 mmol) and [3-(N′-acetyl-hydrazino)-3-oxo-propyl]-carbamic acid tert-butyl ester (0.126 g, 0.514 mmol) are added. The reaction is stirred at room temperature for 18 h then filtered through a Celite™ filter material plug, washing with DCM. The solvent is removed and the residue is purified by chromatography on silica, eluting with EtOAc, to afford the titled compound.

Workup

  1. additionare added
  2. filtrationthen filtered through a Celite™
  3. filtrationfilter material plug
  4. washwashing with DCM
  5. customThe solvent is removed
  6. customthe residue is purified by chromatography on silica
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-cdcd238dbcad48b3a5aae63b48eccee9
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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