Triethylamine → 1-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate

HRID 1360142Notes

Reaction equation

HRID 1360142 reaction equation
C(N(CC)CC)C.[C:8]([N:27]1[CH:31]=[C:30]([CH2:32][OH:33])[N:29]=[CH:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Si:34]([O:41][CH:42]([C:46]1[CH:51]=[CH:50][C:49]([C:52]#[N:53])=[CH:48][CH:47]=1)[C:43](O)=[O:44])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>ClCCl>[Si:34]([O:41][CH:42]([C:46]1[CH:47]=[CH:48][C:49]([C:52]#[N:53])=[CH:50][CH:51]=1)[C:43]([O:33][CH2:32][C:30]1[N:29]=[CH:28][N:27]([C:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:31]=1)=[O:44])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanolHCID 66781710(Tert-butyldimethylsilanyloxy)(4-cyanophenyl)acetic acid

Product 1

HCID 866329551-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.0 mmol of triethylamine and 1.0 mmol propanephosphonic acid cyclic anhydride [68957-94-8](50% in ethyl acetate) are added to a solution of 1.0 mmol of (1-trityl-1H-imidazol-4-yl)methanol [33769-07-2] and 1.0 mmol of (tert-butyldimethylsilanyloxy)(4-cyanophenyl)acetic acid in 20 ml of dichloromethane. The reaction mixture is stirred at room temperature for 3 hours and diluted with dichloromethane. The phases are separated and the organic phase is washed with 1M HCl and brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with 1M HCl and brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-e7b6f41c1a4c4b33bc029be8b69be9e4
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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