Benzhydrylamine → Ethyl (2S,3S)-3-diphenylmethylcarbamoyloxirane-2-carboxylate

HRID 1456610Notes

Reaction equation

HRID 1456610 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[O:8][C@@H:7]1[C:9]([OH:11])=O)=[O:5])[CH3:2].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C.CCCCCC>[C:37]1([CH:36]([NH:35][C:9]([C@H:7]2[O:8][C@@H:6]2[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 7036BenzhydrylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 11030109(2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid

Product 1

HCID 57291692Ethyl (2S,3S)-3-diphenylmethylcarbamoyloxirane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of (2S,3S)-3-ethoxycarbonyloxirane-2-carboxylic acid (8.01 g, 50.0 mmol.) in ethyl acetate (120 mL) was added N-hydroxysuccinimide (5.76 g, 50.0 mmol.) and then added N,N'-dicyclohexylcarbodiimide (5.75 g, 50.0 mmol) under chilling with ice. The resulting mixture was stirred at 5° C. for one hour, and to the mixture was a solution of aminodiphenylmethane (9.17 g, 50.0 mmol.) in ethyl acetate (30 mL). The mixture was stirred at 5° C. for one hour and then at room temperature for one hour. The resulting N,N'-dicyclohexylurea (DC-Urea) was removed by filtration, and the filtrate was washed successively with 1N hydrochloric acid, an aqueous sodium hydrogen carbonate saturated solution, and an aqueous sodium chloride saturated solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystalized from ethyl acetate--n-hexane, to give the desired compound as a white crystalline product (1.25 g, yield: 77%).

Workup

  1. stirringThe mixture was stirred at 5° C. for one hour
  2. waitat room temperature for one hour
  3. customThe resulting N,N'-dicyclohexylurea (DC-Urea) was removed by filtration
  4. washthe filtrate was washed successively with 1N hydrochloric acid
  5. dry with materialan aqueous sodium hydrogen carbonate saturated solution, and an aqueous sodium chloride saturated solution, and then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-320293505c3847a19e7a6b4387c7b2cf
Source dataset
uspto-grants-1998_12
Patent number
US05843992

Reaction notes

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