Hydrochloric Acid → [(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid

HRID 1908302ノート

反応式

HRID 1908302 の反応式
C[O:2][C:3](=[O:21])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)=[O:7].O.O[Li].O.Cl>C1COCC1>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:21])=[O:2])=[O:7])[CH:13]=2)=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24891097[(4-(4-Methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester

生成物 1

HCID 24891149[(4-(4-Methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid収率 12%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [(4-(4-methyl-phenyl)pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 24, (0.092 g, 0.32 mmol) in THF (2 mL) at room temperature is added H2O (1 mL) and LiOH.H2O (0.027 g, 0.64 mmol). The reaction is stirred for 16 hours after which time the solution is acidified using 1M HCl. The solvents are removed under reduced pressure and the solid that remains is suspended in a mixture of THF: MeOH and filtered. The filtrate is concentrated under reduced pressure and the resulting solid is triturated with MeOH and collected by filtration to provide 0.012 g (12% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, MeOD) δ ppm 8.69 (1H, d, J=4.8 Hz), 8.38 (1H, s), 7.86 (1H, d, J=6.2 Hz), 7.72 (2H, d, J=8.1 Hz), 7.38 (1H, d, J=7.9 Hz), 4.21 (1H, s), 2.44 (2H, s). HPLC-MS: m/z 271 [M+H]+.

後処理

  1. customThe solvents are removed under reduced pressure
  2. additionthe solid that remains is suspended in a mixture of THF
  3. filtrationMeOH and filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe resulting solid is triturated with MeOH
  6. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-faae75825864439eb136a1476e93362a
出典データセット
uspto-grants-2013_12
特許番号
US08598210B2

反応ノート

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