Hydrochloric Acid → N-(2-hydroxy-3,5-dichlorobenzoyl)-L-phenylalanine

HRID 1969310Notes

Reaction equation

HRID 1969310 reaction equation
C([O:4][C:5]1[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][C:6]=1[C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])(=O)C.[OH-].[Na+].Cl>C(O)C.O>[Cl:25][C:24]1[C:5]([OH:4])=[C:6]([CH:21]=[C:22]([Cl:26])[CH:23]=1)[C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66906696N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanine

Product 1

HCID 51037939N-(2-hydroxy-3,5-dichlorobenzoyl)-L-phenylalanineYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

One hundred and eight grams of ethyl ester of N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanine were dissolved in 1 L of anhydrous ethyl alcohol and placed in a 2 L round bottomed flask equipped with a magnetic stirring bar and placed in water bath at ambient temperature. Into this mixture a solution of 33.33 g of sodium hydroxide in 37.2 mL of water was added in a single portion and the mixture stirred at ambient temperature for 17 h (overnight). A volume of 68.6 mL of concentrated hydrochloric acid was added under stirring, which was maintained for an additional of 2 h. The precipitated sodium chloride was filtered off and the filtrate evaporated to dryness at 60° C. under 30 T of pressure. The residue of 88.9 g (98% yield) solidified after cooling in form of a colorless glassy product, which was well soluble in toluene or acetonitrile, thereby producing an OTA template (e.g., for use in MIP-OTA production). MS: M+354 and 356 1H NMR (CDCl3, ppm): 12.2 very broad s, 1H, 7.49 d, J 2.4, 1H, 7.35-7.28 m, 3H, 7.20 d, J 2.0, 1H, 7.18-7.16 m, 2H, 6.80 br d, J 6.4, 1H, 6.4 very broad s, 1H, 5.07 dd, 5.2 and 5.2, 1H, 3.34 dd, J 14.0 and 5.2, 1H, 3.27 dd, J 13.6 and 5.2, 1H.

Workup

  1. customplaced in a 2 L round bottomed flask
  2. customequipped with a magnetic stirring bar
  3. customat ambient temperature
  4. stirringunder stirring
  5. temperaturewhich was maintained for an additional of 2 h
  6. filtrationThe precipitated sodium chloride was filtered off
  7. customthe filtrate evaporated to dryness at 60° C. under 30 T of pressure
  8. temperatureafter cooling in form of a colorless glassy product, which
  9. customacetonitrile, thereby producing an OTA template (e.g., for use in MIP-OTA production)

Sources & evidence

ORD record
ord-84f453a5a52947199f62543ea94ce7d0
Source dataset
uspto-grants-2013_04
Patent number
US08426541B2

Reaction notes

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