Diisopropylethylamine → HCID 19024741, compound

HRID 249169Notes

Reaction equation

HRID 249169 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6].Br[CH:28]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=1)[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:32]([O:31][C:29]([CH:28]([C:39]1[CH:40]=[CH:41][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:43][CH:44]=1)[O:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6])=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19024739HCID 19024739, compoundHCID 19024768HCID 19024768, compound

Product 1

HCID 19024741HCID 19024741, compoundYield 165.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 4-[3-(3-hydroxybenzoyl)indol-1yl]butyrate (984 mg), benzyl 2-bromo-2-[4-isobutylphenyl)acetate (362 mg) and diisopropylethylamine (362 mg) in dichloromethane (10 ml) was stirred at 25° C. for 20 hours, and then refluxed for 70 hours. The mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (20 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3-[(benzyloxycarbonyl)(4isobutylphenyl)methoxy]benzoyl]indol-1-yl]butyrate (1.05 g) as an oil.

Workup

  1. temperaturerefluxed for 70 hours
  2. customThe mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (20 g)
  8. washeluting with a mixture of ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-b0a32e148fb848348c43d66b506d8b37
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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