Acetone → HCID 20196874, compound

HRID 652764Notes

Reaction equation

HRID 652764 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([Br:12])[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC(C)C)=O.[CH:29]1([CH2:32][N:33]2[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34]2)[CH2:31][CH2:30]1>O.C(N(CC)CC)C>[CH:29]1([CH2:32][N:33]2[CH2:37][CH2:36][CH:35]([NH:38][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])[C:10]([Br:12])=[CH:11][C:3]=3[O:2][CH3:1])[CH2:34]2)[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 162445651-Cyclopropylmethyl-pyrrolidin-3-ylamineHCID 53854905HCID 53854905, compound

Product 1

HCID 20196874HCID 20196874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

9.3 g of 2-methoxy-4-bromo-5-methylsulphonyl benzoic acid (0.030 mole), 70 ml of acetone, 10 ml of water and 4.2 ml of triethylamine of density 0.72 (0.030 mole) are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. A solution is obtained and cooled to about 0° C. 4.2 g of isobutyl chloroformate (0.030 mole) is added drop by drop, the reaction medium is agitated for 30 minutes with the temperature between 0° and +5° C., then 4.7 g of 1-cyclopropylmethyl-3-aminopyrrolidine (0.033 mole) is poured in drop by drop. The reaction is continued for 2 hours at room temperature then 50 ml of water and 5 ml of soda lye are added. The acetone is evaporated under vacuum and the oil, which is insoluble in water, is extracted twice, each time with 50 ml of methylene chloride. The organic solution is dried over magnesium sulphate and filtered, and the filtrate is evaporated under vacuum. The viscous residue is dissolved hot in 90 ml of isopropanol. The solution is acidified with 7 ml of 6N hydrochloric ethanol. The hydrochloride is crystallised in the refrigerator, then the crystals are filtered, washed with a little isopropanol and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. customA solution is obtained
  3. waitThe reaction is continued for 2 hours at room temperature
  4. customThe acetone is evaporated under vacuum
  5. extractionis extracted twice
  6. dry with materialThe organic solution is dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under vacuum
  9. dissolutionThe viscous residue is dissolved hot in 90 ml of isopropanol
  10. customThe hydrochloride is crystallised in the refrigerator
  11. filtrationthe crystals are filtered
  12. washwashed with a little isopropanol
  13. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-c7d756273dc54307b9b67c9abba78413
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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