Triethylamine → HCID 178460288, compound

HRID 883266Notes

Reaction equation

HRID 883266 reaction equation
Cl[C:2](=[CH2:6])[C:3](O)=[O:4].Cl.Cl.[CH3:9][O:10][C:11](=[O:20])[C@H:12]([CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)[NH2:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:20])[C@H:12]([CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)[NH:13][C:3](=[O:4])[CH:2]=[CH2:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117352-Chloroacrylic acidHCID 178419105HCID 178419105, compound

Product 1

HCID 178460288HCID 178460288, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After chloroacrylic acid (1.6 ml, 20 mmol) was dropped, with ice cooling, into a solution of histidine methyl ester dihydrochloride (6.05 g, 25 mmol) and triethylamine (14 mL, 100 mmol) in methylene chloride (200 mL), the same operation as in the synthesis of N(α)-acryloyl-N(π)-methyl-L-histidine methyl ester was conducted to give N(α)-acryloyl-L-histidine methyl ester (2.0 g, 36%) as an oily product.

Sources & evidence

ORD record
ord-60d9061fa3f543a2a9376bc8387bb8c1
Source dataset
uspto-grants-2012_08
Patent number
US08236844B2

Reaction notes

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