Iodine → HCID 59049654, compound

HRID 1264973Notes

Reaction equation

HRID 1264973 reaction equation
II.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.[CH2:29]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]1[C:45]([NH:47][NH:48][C:49](=O)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:46])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:29]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]1[C:45]1[O:46][C:49]([CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[N:48][N:47]=1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59049684HCID 59049684, compound

Product 1

HCID 59049654HCID 59049654, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 25° C., iodine (3.21, 12.64 mmol) was added to the PPh3 solution in CH2Cl2 (40 mL). After 10 minutes, triethylamine (1.5 mL) was added, followed by compound 71 (2.5 g, 6.32 mmol). After 20 hours, the solution was concentrated and passed through a pad of silica gel (100 mL). The crude oil was purified by column chromatography (25-30% EtOAc in hexanes), affording 600 mg (25%) of the desired product as a solid. 1.6 g of compound 71 was recovered.

Workup

  1. waitAfter 20 hours
  2. concentrationthe solution was concentrated
  3. customThe crude oil was purified by column chromatography (25-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3225c5a73469419799f43ed2795cd71c
Source dataset
uspto-grants-2003_04
Patent number
US06544987B2

Reaction notes

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