Sodium Hydroxide → HCID 69360872, compound

HRID 393444Notes

Reaction equation

HRID 393444 reaction equation
Cl.C[NH:3][C@H:4]([C:23]([OH:25])=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])=[O:14])=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[ClH:21].[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@@H:4]([C:23]([OH:25])=[O:24])[NH2:3])=[CH:7][CH:8]=1)=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69845215HCID 69845215, compound

Product 1

HCID 69360872HCID 69360872, compoundYield 200.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
42.5 °C

Procedure

To a solution of methyl 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine hydrochloride salt (30 mmol, 12.1 g) in ethanol (300 mL) was added 1 N sodium hydroxide (90 mL). The mixture was heated to 40-45° C. for 1 h at which point TLC analysis of the reaction mixture indicated the absence of starting material and it was cooled to room temperature. The solvent was removed under vacuum and the residue was extracted with ether (2×100 mL) to remove neutral impurities. Then, the basic aqueous layer was acidified with 1 N hydrochloric acid to pH 2 to give a clear solution. The solution was lyopholized under high vacuum to afford 11.7 g (100%) of the title compound as a white amorphous solid. HR MS (C16H15Cl3N2O3): Obs. mass, 354.2014. Calcd. mass, 354.2053 (M+H).

Workup

  1. temperaturewas cooled to room temperature
  2. customThe solvent was removed under vacuum
  3. extractionthe residue was extracted with ether (2×100 mL)
  4. customto remove neutral impurities
  5. customto give a clear solution

Sources & evidence

ORD record
ord-d640b66d0aa34eb8916dfe3ac3f5c73e
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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