Water → di-tert-butyl {2-[({[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)amino]-1,3-propanediyl}biscarbamate

HRID 459633Notes

Reaction equation

HRID 459633 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[CH:6]=[N:5]1.[NH2:39][CH:40]([CH2:50][NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46].C(N(CC)CC)C.O>CN(C)C=O>[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:7]([NH:29][C:30]([NH:39][CH:40]([CH2:50][NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:31])[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15186003tert-butyl N-(2-amino-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamateHCID 86597886phenyl [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]carbamate

Product 1

HCID 86597887di-tert-butyl {2-[({[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)amino]-1,3-propanediyl}biscarbamateYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of phenyl [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (1 g) in N,N-dimethylformamide (10 ml) were added di-tert-butyl (2-amino-1,3-propanediyl)biscarbamate (631 mg) and triethylamine (0.83 ml), and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave a crude product, which was triturated with ethyl acetate-diisopropyl ether (1:3). The resulting solid was collected by filtration to give di-tert-butyl {2-[({[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-1,3-propanediyl}biscarbamate (435 mg).

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave a crude product, which
  6. customwas triturated with ethyl acetate-diisopropyl ether (1:3)
  7. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-6530e4ef9e074f529628b30318291b6d
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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