Dicyclohexylcarbodiimide → HCID 86735864, compound

HRID 866995Notes

Reaction equation

HRID 866995 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:25][CH2:26][OH:27])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH3:24])[C:16](=[O:23])[C:17](=[CH:21][CH:22]=2)[C:18]([OH:20])=[O:19])=[CH:10][CH:9]=1)(=[O:7])=[O:6].O[N:29]1[C:33](=[O:34])[CH2:32][CH2:31][C:30]1=[O:35].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:1][CH2:2][CH2:3][N:4]([CH2:25][CH2:26][OH:27])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]([CH3:24])[C:16](=[O:23])[C:17](=[CH:21][CH:22]=2)[C:18]([O:20][N:29]2[C:33](=[O:34])[CH2:32][CH2:31][C:30]2=[O:35])=[O:19])=[CH:12][CH:13]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 22750279HCID 22750279, compound

Product 1

HCID 86735864HCID 86735864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.43 g. of 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-1-methyl-2-oxonicotinic acid and 1.34 g. of N-hydroxysuccinimide in 60 ml. dimethylformamide was cooled in ice and treated dropwise with a solution of 2.56 g. of N,N'-dicyclohexylcarbodiimide in 5 ml. dimethylformamide. The solution was allowed to warm to room temperature over 16 hours. The mixture was cooled and the N,N'-dicyclohexylurea filtered off. Addition of 180 ml. of isopropanol to the filtrate precipitated the 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-1-methyl-2-oxonicotinic acid, 2,5-dioxo-1-pyrrolidinyl ester, which was collected by filtration.

Workup

  1. additiontreated dropwise with a solution of 2.56 g
  2. temperatureThe mixture was cooled
  3. filtrationthe N,N'-dicyclohexylurea filtered off
  4. additionAddition of 180 ml
  5. customof isopropanol to the filtrate precipitated the 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-1-methyl-2-oxonicotinic acid, 2,5-dioxo-1-pyrrolidinyl ester, which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5b94fe4bae264d7a953825dcf48e5e2a
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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