Mandelic Acid → HCID 10492678, compound

HRID 2182118Notes

Reaction equation

HRID 2182118 reaction equation
O[CH:2]([C:6]1[CH:11]=[CH:10]C=[CH:8][CH:7]=1)[C:3](O)=O.[OH2:12].O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.[ClH:23].[CH3:24]N(C)CCCN=C=NCC.CN(C)[CH:37]=[O:38]>C(OCC)(=O)C>[Cl:23][C:22]1[CH:17]=[C:18]([CH:19]=[C:20]([CH3:24])[CH:21]=1)[NH:14][C:10]([CH2:11][C:6]1[CH:7]=[CH:8][C:37]([OH:38])=[CH:3][CH:2]=1)=[O:12]

Participants

6

Reactant 4

HCID 1292Mandelic AcidHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10492678HCID 10492678, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4 hyroxyphenylacetic acid (5.9 g,39 mmol) and 1-hydroxybenzotriazole hydrate (5.8 g,43 mmol) in dimethylformamide (40 mL), 25 (5.5 g, 39 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.0 g,47 mmol) were added. The reaction mixture was stirred overnight at room temperature, then diluted with ethyl acetate (100 mL). The mixture was washed with water (3×50 mL) and 10% potassium hydrogen sulfate (3×50 mL). The organic layers were combined and washed with brine, then dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give a brown oil. Recrystallization from methylene chloride and hexane afforded a beige solid, 6.26 g, 58%. mp 176-178° C.

Workup

  1. washThe mixture was washed with water (3×50 mL) and 10% potassium hydrogen sulfate (3×50 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto give a brown oil
  6. customRecrystallization from methylene chloride and hexane
  7. customafforded a beige solid, 6.26 g, 58%

Sources & evidence

ORD record
ord-79d0b29f63e0480ebb63916dabf27fc9
Source dataset
uspto-grants-2005_05
Patent number
US06894185B2

Reaction notes

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