Water → HCID 68475122, compound

HRID 387662Notes

Reaction equation

HRID 387662 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].O.[Cl-].[Na+].[NH2:15][C:16]1[CH:17]=[C:18]([C:33]([O:35][CH3:36])=[O:34])[C:19]2[CH2:20][N:21]([CH:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])[C:22](=[O:25])[C:23]=2[CH:24]=1>ClCCl>[CH3:7][S:8]([NH:15][C:16]1[CH:17]=[C:18]([C:33]([O:35][CH3:36])=[O:34])[C:19]2[CH2:20][N:21]([CH:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])[C:22](=[O:25])[C:23]=2[CH:24]=1)(=[O:10])=[O:9]

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 68472086HCID 68472086, compound

Product 1

HCID 68475122HCID 68475122, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a three-necked flask, 500 mg of methyl 6-amino-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxylate are dissolved in 5 cm3 of dichloromethane. 150 μl of pyridine are added and the reaction mixture is cooled to a temperature in the vicinity of 0° C. 188 mg of methanesulfonyl chloride are added over 15 min, then the mixture is left to return to a temperature in the vicinity of 25° C. and stirred for 12 h. 5 cm3 of distilled water and 20 cm3 of a saturated solution of sodium chloride are added successively and left stirring for 1 h at a temperature in the vicinity of 25° C. 10 cm3 of dichloromethane are added. The organic phase is separated, dried then concentrated using a rotary evaporator under reduced pressure (5 kPa). The residual yellow solid is triturated with 15 cm3 of hot diisopropyl ether. The mixture is left to return to a temperature in the vicinity of 25° C. The residual solid is filtered, then rinsed with 2×5 cm3 of diisopropyl ether. 574 mg of methyl 6-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxylate are obtained in the form of a beige solid.

Workup

  1. waitthe mixture is left
  2. customto return to a temperature in the vicinity of 25° C.
  3. waitleft
  4. stirringstirring for 1 h at a temperature in the vicinity of 25° C
  5. customThe organic phase is separated
  6. customdried
  7. concentrationthen concentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)
  9. customThe residual yellow solid is triturated with 15 cm3 of hot diisopropyl ether
  10. waitThe mixture is left
  11. customto return to a temperature in the vicinity of 25° C
  12. filtrationThe residual solid is filtered
  13. washrinsed with 2×5 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-e5b0f23a5e8740a7a99a72c8cc41f73c
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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