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

HRID 330203

반응식

HRID 330203 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7fbc992c1416419785df3f8ee6f348a7
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894386

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