Propylamine → Methyl 4-[5-(2-carboxy-1-hydroxy-3-(propylcarbamoyl)propyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330203

反応式

HRID 330203 の反応式
[C:1]([CH:4]1[CH2:8][C:7](=[O:9])[O:6][CH:5]1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH3:21])[CH:14]=[C:13]2[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=1[O:33][CH3:34])([OH:3])=[O:2].C(N(CC)CC)C.[CH2:42]([NH2:45])[CH2:43][CH3:44]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([CH:4]([CH2:8][C:7](=[O:9])[NH:45][CH2:42][CH2:43][CH3:44])[CH:5]([C:10]1[CH:11]=[C:12]2[C:19](=[CH:20][CH:21]=1)[N:15]([CH2:16][CH2:17][CH3:18])[CH:14]=[C:13]2[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=1[O:33][CH3:34])[OH:6])([OH:3])=[O:2]

参加物

6

反応物 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 19870632Methyl 4-[5-(3-carboxy-2,3,4,5-tetrahydro-5-oxofuran-2-yl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

生成物 1

HCID 19870545Methyl 4-[5-(2-carboxy-1-hydroxy-3-(propylcarbamoyl)propyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 4-[5-(3-carboxy-2,3,4,5-tetrahydro-5-oxofuran-2-yl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.89 g), triethylamine (2.1 g), and propylamine (1.5 g) in methylene chloride (15 ml) was stirred and heated under reflux for 22 hr. The cooled mixture was diluted with ethyl acetate, washed (1M hydrochloric acid (twice), water (3 times), brine), dried (MgSO4), and evaporated to give methyl 4-[5-(2-carboxy-1-hydroxy-3-(propylcarbamoyl)propyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.82 g, 82%, as a mixture of diastereomers) as an off-white foam: partial NMR (300 MHz, DMSO-d6): 0.80(m, 6H, 2×CH3, both isomers), 3.83(s, 3H, OCH3, both isomers), 3.92(s, 3H, OCH3, both isomers), 4.71(d, 0.5H, CHOH, isomer A), 5.05(d, 0.5H, CHOH, isomer B), 7.64(t, 0.5H, NH isomer A/B), 7.75(t, 0.5H, NH isomer B/A).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 22 hr
  3. washwashed (1M hydrochloric acid (twice), water (3 times), brine),
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-7fbc992c1416419785df3f8ee6f348a7
出典データセット
uspto-grants-1990_01
特許番号
US04894386

関連ノート

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