Iodine → HCID 57637127, compound

HRID 1804561Notes

Reaction equation

HRID 1804561 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH3:29][CH:30]([CH3:50])[C:31](=[O:49])[CH2:32][NH:33][C:34]([CH2:36][CH2:37][NH:38][C:39](=[O:48])[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=O>ClCCl>[CH:30]([C:31]1[O:49][C:34]([CH2:36][CH2:37][NH:38][C:39](=[O:48])[O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N:33][CH:32]=1)([CH3:50])[CH3:29]

Participants

6

Reactant 4

HCID 807Iodine2×HCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 57637086HCID 57637086, compound

Product 1

HCID 57637127HCID 57637127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100.00 g (215 mmol) PS-triphenylphosphine are suspended in 1000 ml dichloromethane, 59.92 g (236.06 mmol) iodine are added. The mixture is stirred for 0.1 hours at ambient temperature, then 65.32 ml (470.24 mmol) triethylamine are added dropwise. 28.80 g (94.91 mmol) benzyl [2-(3-methyl-2-oxo-butylcarbamoyl)-ethyl]-carbamate dissolved in 200 ml dichloromethane are added. The reaction mixture is stirred for 16 hours at ambient temperature. If the reaction is incomplete, a further 0.1 eq triphenylphosphine and 0.1 eq iodine are added. The mixture is stirred for 16 hours at ambient temperature, then the precipitate is filtered off. The filtrate is evaporated down, the residue is extracted with water and chloroform, the organic phase is dried and evaporated to dryness. The residue is purified by chromatography.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 16 hours at ambient temperature
  3. stirringThe mixture is stirred for 16 hours at ambient temperature
  4. filtrationthe precipitate is filtered off
  5. customThe filtrate is evaporated down
  6. extractionthe residue is extracted with water and chloroform
  7. customthe organic phase is dried
  8. customevaporated to dryness
  9. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-18e5c65d6d754523b84fb4d9ee06d0f7
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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