Hydrochloric Acid → HCID 53693000, compound

HRID 1018655Notes

Reaction equation

HRID 1018655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][CH2:21][NH:22][C:23](=[O:36])[C@@H:24]([NH:28]C(OCCCC)=O)[CH:25]([CH3:27])[CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.Cl.[OH-].[Na+]>C(OCC)C.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][CH2:21][NH:22][C:23](=[O:36])[C@@H:24]([NH2:28])[CH:25]([CH3:27])[CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 57013394HCID 57013394, compound

Product 1

HCID 53693000HCID 53693000, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5.8 g of (S)-2-(butoxycarbonyl-amino)-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1-yloxy)-phenyl}-ethyl]-amide and 5 g of concentrated hydrochloric acid are stirred for 10 minutes in a mixture of 20 ml of diethyl ether and 20 ml of dichloromethane at 0° C. Stirring is continued overnight at room temperature. The reaction mixture is introduced into 100 ml of 2N hydrochloric acid and extraction is carried out twice using 150 ml of diethyl ether each time. The aqueous phase is adjusted to pH 11 with 5M sodium hydroxide. Extraction is then carried out twice using 150 ml of ethyl acetate each time. The organic phases are washed twice with 50 ml of saturated sodium chloride solution each time, dried over sodium sulfate and concentrated, yielding (S)-2-amino-3-methyl-butyric acid N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyn-1-yloxy)-phenyl}-ethyl]-amide, which is recrystallised from ethyl acetate/n-hexane, m.p. 115-117° C.

Workup

  1. extractionExtraction
  2. washThe organic phases are washed twice with 50 ml of saturated sodium chloride solution each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07250fad5f1942a182651b36acdd6626
Source dataset
uspto-grants-2002_11
Patent number
US06482859B1

Reaction notes

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