Trityl chloride → Methyl 3-(1-Tritylimidazol-4-yl) Propionate

HRID 2306221Notes

Reaction equation

HRID 2306221 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[N:4]=[CH:3]1.C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[C:20]1([C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:2]2[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[N:4]=[CH:3]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178500034HCID 178500034, compound

Product 1

HCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of methyl 3-(imidazol-4-yl)propionate hydrochloride, as described above in Step B, (20.2 g, 106 mmol) in dry CHCl3 (500 mL) were added triethylamine (44 mL, 318 mmol), then a solution of triphenylmethyl chloride (29.5 g, 106 mmol) in CHCl3 (100 mL). The mixture was stirred at ambient temperature for 18 hours, then washed with H2O (250 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield the product as a pale solid.

Workup

  1. washwashed with H2O (250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2d74dcffb684bd0b06fda136b6aa34a
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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