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Methanol → (1-Trityl-1H-imidazol-4-yl)acetic acid

HRID 76861
Notes
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Reaction equation

HRID 76861 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:22]1[CH:26]=[C:25]([CH2:27][C:28]([OH:30])=[O:29])[N:24]=[CH:23]1.CO>N1C=CC=CC=1.C(OCC)C>[C:1]([N:22]1[CH:26]=[C:25]([CH2:27][C:28]([OH:30])=[O:29])[N:24]=[CH:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 6456Trityl chlorideHCID 178479752HCID 178479752, compound

Product 1

HCID 11090087(1-Trityl-1H-imidazol-4-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Trityl chloride (51 g, 0.18 mol) is added to a suspension of (1H-imidazol-4-yl)acetic acid hydrochloride (25 g, 0.15 mol) in pyridine (500 mL). This is stirred at room temperature for 16 h, at the end of which MeOH (150 mL) is added. This solution is stirred at room temperature for 1 h. Solvents are evaporated and the residue is taken up in CH2Cl2 and washed with 1 M aqueous citric acid solution (2×) and brine. The organic phase is dried over anhydrous Na2SO4 and evaporated to give a sticky residue which when taken up in diethyl ether and evaporated gave the product as a white solid that is used without further purification. MS (ESI) m/z 368.9 (M+H) (Procedure adapted from J. Org. Chem. 1993, 58, 4606, also prepared in WO2003013526)

Workup

  1. additionis added
  2. customSolvents are evaporated
  3. washwashed with 1 M aqueous citric acid solution (2×) and brine
  4. dry with materialThe organic phase is dried over anhydrous Na2SO4
  5. customevaporated
  6. customto give a sticky residue which when
  7. customevaporated

Sources & evidence

ORD record
ord-a53f227d0aa2401cb60c378457e91a42
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes