Hydrochloric Acid → HCID 70145902, compound

HRID 849670Notes

Reaction equation

HRID 849670 reaction equation
[C-:1]#[N:2].[K+].[C:4]1([C@@H:10]([NH2:19])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:20]([C:22]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]1)=O.Cl>C(O)C.O>[C:1]([CH:20]([NH:19][C@H:10]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[C:22]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 10160531(S)-1-Phenyl-2-(p-tolyl)ethylamine

Product 1

HCID 70145902HCID 70145902, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

An eggplant type flask was charged with 133 mg of potassium cyanide, 1.0 g of (S)-1-phenyl-2-p-tolylethylamine and 1 ml of water. After adding 146 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2.5 ml of ethanol, dropwise at room temperature, the resulting mixture was further mixed with 0.2 ml of concentrated hydrochloric acid, and stirred for 1 hour at the same temperature and then for 2 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 251 mg (67%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was found to be 4:1 based on the integral ratio of NMR.

Workup

  1. waitfor 2 hours at 50° C
  2. customcompletion of the reaction
  3. extractionextracted with ethyl acetate
  4. washNext, the resulting organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing insoluble matter
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-56d6855143874f09ac395eec45b6cbec
Source dataset
uspto-grants-2000_01
Patent number
US06013806

Reaction notes

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