1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [(4-Iodo-pyridine-2-carbonyl)amino]-acetic acid methyl ester

HRID 2188528Notes

Reaction equation

HRID 2188528 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH2:37]>C(Cl)Cl>[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH:37][C:8]([C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][N:5]=1)=[O:10]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 8182784-Iodopyridine-2-carboxylic acid

Product 1

HCID 59513095[(4-Iodo-pyridine-2-carbonyl)amino]-acetic acid methyl esterYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodo-picolinic acid (1.41 g, 5.66 mmol) in CH2Cl2 (35 mL) at room temperature under N2 is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (1.62 g, 8.49 mmol) and 1-hydroxybenzotriazole (HOBt) (0.077 g, 0.57 mmol). The solution is stirred for 5 minutes and glycine methyl ester hydrochloride (1.07 g, 8.49 mmol) is added and the reaction is stirred 16 hours. The reaction volume is concentrated under reduced pressure and the crude material was partitioned between EtOAc and 1M K2CO3. The aqueous phase is removed and the organic phase washed with H2O, sat. NaCl, dried (MgSO4), filtered and concentrated under reduced pressure to afford a brown oil which is purified over silica (EtOAc:heptane gradient 1:4) to afford 0.805 g (44% yield) of the desired product as a colorless solid. HPLC-MS: m/z 321 [M+H]+.

Workup

  1. stirringthe reaction is stirred 16 hours
  2. concentrationThe reaction volume is concentrated under reduced pressure
  3. customthe crude material was partitioned between EtOAc and 1M K2CO3
  4. customThe aqueous phase is removed
  5. washthe organic phase washed with H2O, sat. NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a brown oil which
  10. customis purified over silica (EtOAc:heptane gradient 1:4)

Sources & evidence

ORD record
ord-4d9a0a7c8c634ecabb4b505f65e683ac
Source dataset
uspto-grants-2012_12
Patent number
US08323671B2

Reaction notes

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