2,5-Dichlorobenzoic acid → HCID 54433102, compound

HRID 1634027Notes

Reaction equation

HRID 1634027 reaction equation
[F-].[K+].Br[CH2:4][C:5](=[O:23])[C@@H:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27]([OH:29])=[O:28].C(OCC)(=O)C>CN(C=O)C>[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27]([O:29][CH2:4][C:5](=[O:23])[C@@H:6]([NH:15][C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:28]

Participants

6

Reactant 4

HCID 57842,5-Dichlorobenzoic acidHCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 53747170HCID 53747170, compound

Product 1

HCID 54433102HCID 54433102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium fluoride (0.326 g, 5.61 mmol) was added to a mixture of the tert-butyl (S)-3-bromo-2-oxo-1-phenethylpropylcarbamate (1.00 g, 2.81 mmol) and 2,5-dichlorobenzoic acid (1.07 g, 5.61 mmol) in DMF (10 mL). The mixture was stirred for 2 hours at room temperature and then ethyl acetate (75 mL) was added. The solution was washed with 1M hydrochloric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL), dried (MgSO4), filtered, and evaporated to dryness to provide crude (S)-3-tert-butoxycarbonylamino-2-oxo-5-phenylpentyl 2,5-dichlorobenzoate.

Workup

  1. washThe solution was washed with 1M hydrochloric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-835182c4c9de422f9582a142502d10c7
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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