Trityl chloride → 4-(tert-butoxycarbonylaminomethyl)-5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazole

HRID 349579Notes

Reaction equation

HRID 349579 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N([CH2:44][CH3:45])CC)C>CN(C)C=O.C(OCC)(=O)C>[C:15]([O:14][C:12]([NH:11][CH2:10][C:3]1[CH:4]=[N:5][N:6]([CH2:7][CH2:8][O:9][C:25]([C:45]2[CH:44]=[CH:37][CH:32]=[CH:33][CH:34]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:2]=1[NH:1][C:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 179619715-amino-4-(tert-butoxycarbonylaminomethyl)-1-(2-hydroxyethyl)-1H-pyrazole

Product 1

HCID 179620244-(tert-butoxycarbonylaminomethyl)-5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-amino-4-(tert-butoxycarbonylaminomethyl)-1-(2-hydroxyethyl)-1H-pyrazole (243 g) in N,N-dimethylformamide (1.82 L) was added triphenylmethyl chloride (581 g), triethylamine (452 ml) and N,N-dimethylaminopyridine (9.91 g) successively. The reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water (twice) and brine, dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography to give 4-(tert-butoxycarbonylaminomethyl)-5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazole, which was crystallized from diisopropyl ether/hexane (1:2). The resulting crystals were collected by filtration on a glass filter, washed with diisopropyl ether/hexane (1:2) and dried in vacuo to give the objective compound (480 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (twice) and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1369a873a20e4731a5b8e89b88d82769
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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