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

HRID 1430196ノート

反応式

HRID 1430196 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-7a8c7a391ec549619d05a6005dc71e71
出典データセット
uspto-grants-2015_01
特許番号
US08940773B2

反応ノート

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