N,N'-Dicyclohexylurea → HCID 131714264, compound

HRID 371201Notes

Reaction equation

HRID 371201 reaction equation
[CH3:1][S:2][C:3](=[S:15])[S:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([OH:8])=O.[CH2:16]([N+:20]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].[NH2:33][CH:34]1[CH2:37][N:36]([S:38]([O-:41])(=[O:40])=[O:39])[C:35]1=[O:42].C1(N=C=NC2CCCCC2)CCCCC1.C1(NC(=O)NC2CCCCC2)CCCCC1>C(#N)C>[CH2:29]([N+:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31][CH3:32].[CH3:1][S:2][C:3](=[S:15])[S:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([NH:33][C@H:34]1[CH2:37][N:36]([S:38]([O-:41])(=[O:40])=[O:39])[C:35]1=[O:42])=[O:8]

Participants

6

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 12494113HCID 12494113, compoundHCID 133095013-Amino-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 131714264HCID 131714264, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1.03 g of (±)-α-[[(methylthio)thioxomethyl]thio]benzeneacetic acid and 1.63 g of 3-amino-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt (see Example 6A) in 30 ml of acetonitrile is treated with 0.8 g of dicyclohexylcarbodiimide dissolved in 10 ml of acetonitrile at -5° C. After stirring for about 16 hours the formed dicyclohexyl urea is filtered off and the mother liquor is evaporated. The remaining oily residue is chromatographed on a column of 400 g of silica (ethyl/acetate/methanol/water (8.5:1:0.5) is the eluent), yielding 1.3 g of the title compound.

Workup

  1. filtrationis filtered off
  2. customthe mother liquor is evaporated
  3. customThe remaining oily residue is chromatographed on a column of 400 g of silica (ethyl/acetate/methanol/water (8.5:1:0.5)

Sources & evidence

ORD record
ord-7b2359e0f88941388ba976f4b66cbeab
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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