Dicyclohexylcarbodiimide → N-[2-(4,6-Dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamid

HRID 344581Notes

Reaction equation

HRID 344581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12]([OH:14])=O)[N:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:30][O:31][C:32]([C:34]1[CH:44]=[CH:43][CH:42]=[CH:41][C:35]=1[CH2:36][S:37]([NH2:40])(=[O:39])=[O:38])=[O:33]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([CH2:11][C:12]([NH:40][S:37]([CH2:36][C:35]2[CH:41]=[CH:42][CH:43]=[CH:44][C:34]=2[C:32]([O:31][CH3:30])=[O:33])(=[O:38])=[O:39])=[O:14])[N:6]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 124207552-(4,6-Dimethoxypyrimidin-2-yl)acetic acidHCID 13958774Benzoic acid, 2-[(aminosulfonyl)methyl]-, methyl ester

Product 1

HCID 14580665N-[2-(4,6-Dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.9 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid in 40 ml of absolute dichloromethane is added dropwise at 0° C. to 2° C. to a solution of 1.9 g of dicyclohexylcarbodiimide, 100 mg of 4-dimethylaminopyridine and 2.1 g of 2-methoxycarbonylbenzylsulfonamide in 40 ml of absolute dichloromethane. Stirring is continued for 1 hour at 0° C., and the mixture is allowed to come to room temperature and stirred for another 0.5 hour. The solids are filtered off, and the filtrate is concentrated in a rotary evaporator. 100 ml of 2 N sodium carbonate solution are added to the residue, the mixture is stirred for 0.5 hour at room temperature, and the solids are filtered off with suction. The sodium carbonate alkaline phase is extracted twice using diethyl ether, and a pH of 2-3 is established using concentrated hydrochloric acid. Stirring is continued for 15 minutes, the solids are filtered off with suction, the filter residue is washed once with water and twice with ether, and dried in vacuo. This gives 2.4 g of N-[2-(4,6-dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamide of melting point 98°-101° C.

Workup

  1. customto come to room temperature
  2. stirringstirred for another 0.5 hour
  3. filtrationThe solids are filtered off
  4. concentrationthe filtrate is concentrated in a rotary evaporator
  5. addition100 ml of 2 N sodium carbonate solution are added to the residue
  6. stirringthe mixture is stirred for 0.5 hour at room temperature
  7. filtrationthe solids are filtered off with suction
  8. extractionThe sodium carbonate alkaline phase is extracted twice using diethyl ether
  9. stirringStirring
  10. waitis continued for 15 minutes
  11. filtrationthe solids are filtered off with suction
  12. washthe filter residue is washed once with water and twice with ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-5948eeb5f41145369882c9a1481ba0a4
Source dataset
uspto-grants-1991_10
Patent number
US05053072

Reaction notes

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