Trityl chloride → tert-butyl (5S)-5-([3-(tert-butoxycarbonylamino)propionyl]amino}-6-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-6-oxohexylcarbamate

HRID 459647Notes

Reaction equation

HRID 459647 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:36])[C@@H:10]([NH:23][C:24](=[O:35])[CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[C:44]1([C:50](Cl)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)(Cl)Cl>[C:31]([O:30][C:28]([NH:27][CH2:26][CH2:25][C:24]([NH:23][C@H:10]([C:9]([NH:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:50]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:36])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:35])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 86597899HCID 86597899, compound

Product 1

HCID 86597900tert-butyl (5S)-5-([3-(tert-butoxycarbonylamino)propionyl]amino}-6-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-6-oxohexylcarbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the crude product of tert-butyl (5S)-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-5-{[3-(tert-butoxycarbonylamino)propionyl]amino}-6-oxohexylcarbamate and triethylamine (0.50 g) in chloroform (30 ml) was added triphenylmethyl chloride (1.37 g), and the mixture was stirred at room temperature for 16 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-{[3-(tert-butoxycarbonylamino)propionyl]amino}-6-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-6-oxohexylcarbamate (1.62 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-f4e4bc8cfc5a471898c6cd4b734f86aa
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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