Water → tert-butyl [(3S)-3-hydroxy-4-oxo-4-((5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl)amino)butyl]carbamate

HRID 459628Notes

Reaction equation

HRID 459628 reaction equation
[OH:1][C@H:2]([C:13]([NH:15][C:16]1[CH:17]=[N:18][N:19]([CH2:41][CH2:42][OH:43])[C:20]=1[NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:44](Cl)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(N(CC)CC)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:1][C@H:2]([C:13](=[O:14])[NH:15][C:16]1[CH:17]=[N:18][N:19]([CH2:41][CH2:42][O:43][C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:20]=1[NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 69651947tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate

Product 1

HCID 69651992tert-butyl [(3S)-3-hydroxy-4-oxo-4-((5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl)amino)butyl]carbamateYield 42.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate (2.5 g) in N,N-dimethylformamide (25 ml) were added trityl chloride (1.25 g), triethylamine (1.78 ml) and 4-dimethylaminopyridine (52.1 mg), and the mixture was stirred for 1 hour. The reaction mixture was warmed up to 60° C. and stirred at the same temperature for 2 days. Water was added to the 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 an oil, which was purified by column chromatography on silica gel (methylene chloride:ethyl acetate=5:1) to give tert-butyl [(3S)-3-hydroxy-4-oxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate (1.5 g).

Workup

  1. stirringstirred at the same temperature for 2 days
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure
  6. customgave an oil, which
  7. customwas purified by column chromatography on silica gel (methylene chloride:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-18b1f41a55f9437aa2958e3999ff71ab
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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