Acetone → HCID 86741592, compound

HRID 652779Notes

Reaction equation

HRID 652779 reaction equation
CO[C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([S:13](CC)(=[O:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=O.C[C:19]([CH3:21])=O.Cl[C:23](OCC(C)C)=[O:24].[CH:30]1([CH2:36][N:37]2[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O.C(N(CC)CC)C>[CH:30]1([CH2:36][N:37]2[CH2:41][CH2:40][CH:39]([NH:42][C:5](=[O:7])[C:4]3[CH:8]([O:24][CH3:23])[C:9](=[S:13](=[O:14])=[O:15])[C:10]([NH2:12])=[C:11]([CH2:19][CH3:21])[CH:3]=3)[CH2:38]2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 30182324-Amino-5-(ethylsulfonyl)-2-methoxybenzoic acidHCID 218906401-(Cyclohexylmethyl)pyrrolidin-3-amine

Product 1

HCID 86741592HCID 86741592, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

7.8 g of 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid, 70 ml of acetone, 10 ml of water and 3 g of triethylamine are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The mixture is cooled to 0° C. and 4.1 g of isobutyl chloroformate is poured in drop by drop. It is agitated for 45 minutes at 0° C. and 6 g of 1-cyclohexylmethyl-3-amino-pyrrolidine is dripped in. The reaction is continued for 2 hours at room temperature, 80 ml of water and 5 ml of soda lye are added, then the acetone is evaporated under vacuum. An oil is decanted; it is washed twice with 100 ml of water than dissolved hot in 50 ml ethyl acetate. It is chilled in a refrigerator. The crystals are filtered off, washed with a little ethyl acetate then dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. waitThe reaction is continued for 2 hours at room temperature
  3. customthe acetone is evaporated under vacuum
  4. customAn oil is decanted
  5. washit is washed twice with 100 ml of water
  6. dissolutionthan dissolved hot in 50 ml ethyl acetate
  7. temperatureIt is chilled in a refrigerator
  8. filtrationThe crystals are filtered off
  9. washwashed with a little ethyl acetate
  10. customthen dried in an oven at 50° C.

Sources & evidence

ORD record
ord-af554a65b7584f12b9b65bc91abfaa7a
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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