Trityl chloride → HCID 22001652, compound

HRID 324988Notes

Reaction equation

HRID 324988 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([C:24]1[CH:25]=[C:26]2[C:31](=[O:32])[NH:30][C:28](=[O:29])[C:27]2=[CH:33][CH:34]=1)([OH:23])=[O:22].CCN(C(C)C)C(C)C>C(#N)C>[C:1]([N:30]1[C:31](=[O:32])[C:26]2=[CH:25][C:24]([C:21]([OH:23])=[O:22])=[CH:34][CH:33]=[C:27]2[C:28]1=[O:29])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 88439Trimellitimide

Product 1

HCID 22001652HCID 22001652, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To trityl chloride resin (5 g; 10.25 retool; 200-400 mesh: 1% divinylbenzene-crosslinked polystyrene) presoaked in 80 mL dry acetonitrile for 30 min., 5 g (26 mmol) 4-carboxyphthalimide (2) from Example 2 and 6 mL (34 mmol) DIPEA were added, and the suspension was refluxed for 72 h. Following filtration, the polymer was washed with 300 mL DMF and then 300 mL CH2Cl2. The loading was determined by weight difference, and confirmed to be 0.5 mmol/g resin by TFA-induced cleavage of 4-carboxyphthalimide from the resin.

Workup

  1. temperaturethe suspension was refluxed for 72 h
  2. filtrationfiltration
  3. washthe polymer was washed with 300 mL DMF

Sources & evidence

ORD record
ord-b1d1cd74b8454c1a83d54ec1e78088b1
Source dataset
uspto-grants-2001_04
Patent number
US06221877B1

Reaction notes

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