Trityl chloride → HCID 178481897, compound

HRID 459648Notes

Reaction equation

HRID 459648 reaction equation
[C:1]([O:5][C:6]([N:8]=[C:9]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[NH:10][C@H:11]([C:24]([NH:26][C:27]1[CH:28]=[N:29][N:30]([CH3:33])[C:31]=1[NH2:32])=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:49]1([C:55](Cl)([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]=[C:9]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[NH:10][C@H:11]([C:24]([NH:26][C:27]1[CH:28]=[N:29][N:30]([CH3:33])[C:31]=1[NH:32][C:55]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178481896HCID 178481896, compound

Product 1

HCID 178481897HCID 178481897, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the crude product tert-butyl (5S)-5-[2,3-bis(tert-butoxycarbonyl)guanidino]-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-6-oxohexylcarbamate and triethylamine (1.01 g) in chloroform (100 ml) was added triphenylmethyl chloride (2.78 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform to give tert-butyl (5S)-5-[2,3-bis(tert-butoxycarbonyl)guanidino]-6-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-6-oxohexylcarbamate (5.60 g) as an oil.

Workup

  1. washThe reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform

Sources & evidence

ORD record
ord-5ec05e980be74873b3a3c2a843ff5ea6
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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