Ethyl Acetate → HCID 19029316, compound

HRID 2256306Notes

Reaction equation

HRID 2256306 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][C:22](OC)=[CH:21]C=2)=[O:16])[CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].[BH4-].[Na+].[CH3:41]COC(C)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:13])[CH2:14][C:15]([N:17]([CH3:41])[C:18]2[CH:19]=[CH:24][C:23]([O:28][CH3:27])=[CH:22][CH:21]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 70193309HCID 70193309, compound

Product 1

HCID 19029316HCID 19029316, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dichloro-beta-[2-[(4-methoxyphenyl)methylamino]-2-oxoethyl]benzenepropanoic acid (7.2 g) in EtOAc (125 mL) was treated with carbonyldiimidazole (4.4 g) and N,N-dimethylaminopyridine (0.22 g). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for one hour. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (4.46 g) in H2O (75 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with EtOAc (100 mL) and washed with H2O (100 mL), 1N HCl (100 mL), and H2O (100 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 60-100% EtOAc/hexane gave the title compound (5.43 g).

Workup

  1. temperatureheated at 50° C. for one hour
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with H2O (100 mL), 1N HCl (100 mL), and H2O (100 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an oil
  10. washSilica gel chromatography eluting with 60-100% EtOAc/hexane

Sources & evidence

ORD record
ord-af1742e89f3e473db0eb06d76754724a
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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