1,1'-Carbonyldiimidazole → HCID 19029331, compound

HRID 2256290Notes

Reaction equation

HRID 2256290 reaction equation
[C:1]1([CH2:7][NH:8][C:9](=[O:22])[CH2:10][CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:5][CH:4]=[CH:3]C=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.O.CCOCC>[OH:15][CH2:13][CH2:12][CH:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:10][C:9]([N:8]([CH3:23])[C:7]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=1)=[O:22]

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 70196436HCID 70196436, compound

Product 1

HCID 19029331HCID 19029331, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Beta-[2-[(phenyl)methylamino]-2-oxoethyl]benzenepropanoic acid (11.5 g) in EtOAc (225 mL) was treated with carbonyldiimidazole (11.68 g) and N,N-dimethylaminopyridine (1.0 g). 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 (9.74 g) in H2O (150 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with Et2O and washed with 1N HCl (100 mL), sat. NaHCO3 (100 mL) and water (100 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound (10.4 g).

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 (100 mL), sat. NaHCO3 (100 mL) and water (100 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87f8f503cb1343ddb1bcf12883f7acdc
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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