Dicyclohexylcarbodiimide → HCID 86735861, compound

HRID 866992Notes

Reaction equation

HRID 866992 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:24][CH2:25][OH:26])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][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:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:1][CH2:2][CH2:3][N:4]([CH2:24][CH2:25][OH:26])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[NH:15][C:16](=[O:23])[C:17](=[CH:21][CH:22]=2)[C:18]([O:20][N:28]2[C:32](=[O:33])[CH2:31][CH2:30][C:29]2=[O:34])=[O:19])=[CH:12][CH:13]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 22750276HCID 22750276, compound

Product 1

HCID 86735861HCID 86735861, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 45 g. of 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-2-oxonicotinic acid and 14.0 g. of N-hydroxysuccinimide in 450 ml. of dimethylformamide is cooled to 0°-5° C. and treated dropwise, with stirring, with a solution of 26.8 g. of N,N'-dicyclohexylcarbodiimide in 30 ml. of dimethylformamide. The mixture is stirred for 16 hours at room temperature, then cooled and filtered to remove by-product N,N'-dicyclohexylurea. The filtrate is diluted with 1.5 l. of 2-propanol and the resulting precipitate of 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-2-oxonicotinic acid, 2,5-dioxo-1-pyrrolidinyl ester is collected by filtration, washed with cold 2-propanol and dried; m.p. 213°-215.5° C.

Workup

  1. additiontreated dropwise
  2. stirringThe mixture is stirred for 16 hours at room temperature
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove by-product N,N'-dicyclohexylurea
  6. additionThe filtrate is diluted with 1.5 l
  7. filtrationof 2-propanol and the resulting precipitate of 6-[4-[bis(2-hydroxyethyl)aminosulfonyl]phenyl]-1,2-dihydro-2-oxonicotinic acid, 2,5-dioxo-1-pyrrolidinyl ester is collected by filtration
  8. washwashed with cold 2-propanol
  9. customdried

Sources & evidence

ORD record
ord-cf4209dd04954a2091b28795992bb546
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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