Hydrochloric Acid → FK 143

HRID 249167Notes

Reaction equation

HRID 249167 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=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]([OH:21])=[O:20])[CH:8]=1)=[O:6].[CH2:25]([C:29]1[CH:34]=[CH:33][C:32]([CH:35](Cl)[C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)=[CH:31][CH:30]=1)[CH:26]([CH3:28])[CH3:27].C(N(C(C)C)CC)(C)C.Cl>ClCCl>[CH2:42]([C:39]1[CH:40]=[CH:41][C:36]([CH:35]([NH:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:8]=2)=[O:6])[C:32]2[CH:33]=[CH:34][C:29]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:30][CH:31]=2)=[CH:37][CH:38]=1)[CH:43]([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 11131084HCID 11131084, compoundHCID 19010817Bis(4-isobutylphenyl)chloromethane2×

Product 1

HCID 178077FK 143Yield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (880 mg), bis(4-isobutylphenyl)methyl chloride (1.03 g) and diisopropylethylamine (0.945 g) in dichloromethane (20 ml) was stirred at 25° C. overnight, and bis(4-isobutylphenyl)methyl chloride (170 mg) and diisopropylethylamine (86 mg) were added thereto. After stirring at 25° C. for 3 hours, the reaction mixture was poured into cold 1N hydrochloric acid. The organic layer was separated, washed with water, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (100 g) with a mixture of chloroform and methanol (50:1) as eluent and freeze-dried from benzene to give 4-[3-[3-(bis[4-isobutylphenyl)methylamino]benzoyl]indol-1-yl]butyric acid (820 mg) as pale yellow powder.

Workup

  1. stirringAfter stirring at 25° C. for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (100 g) with a mixture of chloroform and methanol (50:1) as eluent
  7. dry with materialfreeze-dried from benzene

Sources & evidence

ORD record
ord-17efa2c6c99440988fb2363693c22d68
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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