Acetic Acid → HCID 23550121, compound

HRID 1633901Notes

Reaction equation

HRID 1633901 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)[CH3:2].[CH:19]1([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:29][C:28]2[CH:30]=[CH:31][C:25]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:26][CH:27]=2)=[CH:11][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 807644-CyclohexylbenzenamineHCID 5003444Sodium cyanoborohydrideHCID 225021083-(4-Formylbenzoylamino)propionic acid ethyl ester

Product 1

HCID 23550121HCID 23550121, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a well stirred solution of 3-(4-formylbenzoylamino)propionic acid ethyl ester (13.8 g, 55.3 mmol) in ethanol (150 mL) was added a solution of 4-cyclohexylaniline (9.70 g, 55.3 mmol) in ethanol (75 mL). The mixture was heated to reflux for 30 minutes, and then acetic acid (50 mL) and sodium cyanoborohydride (3.50 g, 55.5 mmol) were added. After 10 minutes of additional heating, the mixture was cooled on an ice-bath. The solid precipitate was collected by filtration, washed several times with cold water and dried in a vacuum oven overnight to afford 18.16 g (80%) of 3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}propionic acid ethyl ester.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture was cooled on an ice-bath
  4. filtrationThe solid precipitate was collected by filtration
  5. washwashed several times with cold water
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-2b2c1e01a64249079031d4211f98b55f
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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