Dichloromethane → HCID 19870586, compound

HRID 330207Notes

Reaction equation

HRID 330207 reaction equation
[OH:1][CH:2]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])[CH:3]([C:6](=[O:11])[NH:7][CH2:8][CH2:9][CH3:10])[CH2:4][CH3:5].[C:37](OC(=O)C)(=[O:39])[CH3:38].C(N(CC)CC)C.C(Cl)Cl>C(OCC)(=O)C>[C:37]([O:1][CH:2]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])[CH:3]([C:6](=[O:11])[NH:7][CH2:8][CH2:9][CH3:10])[CH2:4][CH3:5])(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19870644HCID 19870644, compound

Product 1

HCID 19870586HCID 19870586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-[5-[1-hydroxy-2-(propylcarbamoyl)butyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.75 g, as a mixture of diastereomers) was combined with acetic anhydride (0.31 g), triethylamine (0.152 g), and methylene chloride (20 ml), under a nitrogen atmosphere, and the mixture heated under reflux for 20 hr. The cooled mixture was diluted with ethyl acetate, washed (1M hydrochloric acid (twice), water, brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 8:2 methylene chloride:ethyl acetate, to give methyl 4-[5-[1-acetoxy-2-(propylcarbamoyl)butyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.69 g, 85%, as a mixture of diastereomers) as an oil: partial NMR (300 MHz, DMSO-d6): 0.40(t, 3H, CH3, one isomer), 0.66(t, 3H, CH3, other isomer), 0.79(m, 12H, 2×CH3, one isomer, 2×CH3, other isomer), 1.84(s, 3H, OCOCH3, one isomer), 1.97(s, 3H, OCOCH3, other isomer), 5.66 (d, 1H, CHOCOCH3, one isomer), 5.79(d, 1H, CHOCOCH3, other isomer), 7.67(br t, 1H, NH, one isomer), 8.04(br t, 1H, NH, other isomer).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 20 hr
  3. washwashed (1M hydrochloric acid (twice), water, brine),
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a dark oil
  7. customThe product was purified by flash chromatography
  8. washeluting with 8:2 methylene chloride

Sources & evidence

ORD record
ord-f89a9a494f3748808058a31be1389c3f
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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