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

HRID 330203

Reaction equation

HRID 330203 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7fbc992c1416419785df3f8ee6f348a7
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Linked notes

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