Citric Acid → HCID 67005271, compound

HRID 563140Notes

Reaction equation

HRID 563140 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([N:12]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:30][CH:29]=1)[C:13](=[O:26])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:34]([C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:12]([C:13](=[O:26])[CH:14]=[CH:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=2)[C@@H:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:39])=[O:2])=[CH:29][CH:30]=1)[CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 67005474HCID 67005474, compound

Product 1

HCID 67005271HCID 67005271, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{(4-pentyl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-(S)-3-phenyl-propionic acid methyl ester (6.6 g, 12.3 mmol) was dissolved in MeOH (150 mL) and 1M NaOHaq. (25 mL) was added. Stirring was continued for 1 h. A solution of 10% citric acid was added till the pH=6, followed by removal of the MeOH under reduced pressure and the addition of NaCl (solid) to saturate the solution. The product was extracted with EtOAc (2×150 mL). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to give 6.55 g (quant. yield) of 2-{(4-pentyl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-(S)-3-phenyl-propionic acid. LC-MS: tR=1.16 min; [M+H]+=524.38.

Workup

  1. addition(25 mL) was added
  2. customfollowed by removal of the MeOH under reduced pressure
  3. additionthe addition of NaCl (solid)
  4. concentrationto saturate the solution
  5. extractionThe product was extracted with EtOAc (2×150 mL)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6e67cc88d564c4da2d62f7c91b2f1b5
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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