1,1'-Carbonyldiimidazole → HCID 19029318, compound

HRID 2256276Notes

Reaction equation

HRID 2256276 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21]C=2)=[O:16])[CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:25](N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.O.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:13])[CH2:14][C:15]([N:17]([CH3:25])[C:18]2[CH:19]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 70196492HCID 70196492, compound

Product 1

HCID 19029318HCID 19029318, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dichloro-beta-[2-[(phenyl)methylamino]-2-oxoethyl]benzenepropanoic acid (0.98 g) in EtOAc (25 mL) was treated with carbonyldiimidazole (0.653 g) and N,N-dimethylaminopyridine (trace). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for two hours. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (0.668 g) in H2O (10 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with Et2O and washed with 1N HCl (20 mL), sat. NaHCO3 (20 mL) and water (20 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound (0.908 g). Mass spectrum (CI): 352.

Workup

  1. temperatureheated at 50° C. for two hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with 1N HCl (20 mL), sat. NaHCO3 (20 mL) and water (20 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-975f2f1123a44af8a62fcd9d98260b68
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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