2,6-Dichlorobenzoic acid → HCID 70145404, compound

HRID 397460Notes

Reaction equation

HRID 397460 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[F-].[K+].[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH3:24])=[C:16]1[C:25]([NH:27][C@H:28]([C:32]([NH:34][CH:35]([C:44](=[O:47])[CH2:45]Br)[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26]>>[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH3:24])=[C:16]1[C:25]([NH:27][C@H:28]([C:32]([NH:34][CH:35]([C:44](=[O:47])[CH2:45][O:5][C:4](=[O:6])[C:3]1[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:11])[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:26]

Participants

4

Reactant 3

HCID 57582,6-Dichlorobenzoic acidHCID 522689Potassium FluorideHCID 86584478HCID 86584478, compound

Product 1

HCID 70145404HCID 70145404, compoundYield 79%

Procedure

To a mixture of 2,6-dichlorobenzoic acid (0.023 g, 0.12 mmol) and potassium fluoride (0.015 g, 0.25 mmol) at room temperature under nitrogen was added N-[(1,3-dimethyl-indole-2-carbonyl)valinyl]-3-amino-5-bromo-4-oxo-pentanoic acid, tert-butyl ester (0.054 g, 0.10 mmol) in one portion. After stirring at room temperature for further 16 hrs, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated NaHCO3 solution, and brine, dried over sodium sulfate, and concentrated. Trituration with ether gave the title compound as a white powder (0.051 g, 79%). TLC(CH2Cl2/MeOH, 95/5): Rf=0.88.

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, saturated NaHCO3 solution, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a1fc04202d84e74834bedbef65b998e
Source dataset
uspto-grants-2003_08
Patent number
US06610683B2

Reaction notes

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