Ethyl 3-(methylamino)propanoate → 3-{Methyl[(3-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoic acid

HRID 1877131ノート

反応式

HRID 1877131 の反応式
C[C:2]1[CH:10]=[C:9]([NH:11][CH:12]([C:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:18]=2[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:29][NH:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34].Cl.[CH2:39](N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:29][N:30]([C:4]([C:3]1[CH:7]=[CH:8][C:9]([NH:11][CH:12]([C:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:18]=2[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:10]([CH3:39])[CH:2]=1)=[O:5])[CH2:31][CH2:32][C:33]([OH:35])=[O:34]

参加物

8

反応物 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68509237HCID 68509237、化合物HCID 178526939HCID 178526939、化合物

生成物 1

HCID 595294323-{Methyl[(3-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoic acid収率 97%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}benzoic acid (228 mg), ethyl 3-(methylamino)propanoate (94 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg), hydroxybenzotriazole monohydrate (110 mg) and triethylamine (100 μL) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 4 hr. Ethyl acetate was added, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure. To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.2 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (271 mg, 97%).

後処理

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.2 mL)
  7. customThe solvent was evaporated under reduced pressure, and water (10 mL)
  8. additionwas added
  9. temperaturecooling
  10. stirringstirred for 1 hr
  11. filtrationThe resulting precipitate was collected by filtration
  12. customdried

出典と根拠

ORDレコード
ord-e3d7ce69aa0545c38b898bdb6576be7d
出典データセット
uspto-grants-2012_11
特許番号
US08309580B2

反応ノート

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