Dicyclohexylcarbodiimide → HCID 15017682, compound

HRID 2352089Notes

Reaction equation

HRID 2352089 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32](=[O:34])[CH3:33])/[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:60][CH:61]1[C:91](=[O:92])[N:63]2[C:64]([C:75]([O:77][CH:78]([C:85]3[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=3)[C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)=[O:76])=[C:65](/[CH:68]=[CH:69]\[CH2:70][O:71][C:72](=[O:74])[CH3:73])[CH2:66][S:67][C@H:62]12>C1COCC1.CCOC(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32](=[O:34])[CH3:33])/[C:27]([NH:60][CH:61]2[C:91](=[O:92])[N:63]3[C:64]([C:75]([O:77][CH:78]([C:79]4[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=4)[C:85]4[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=4)=[O:76])=[C:65](/[CH:68]=[CH:69]\[CH2:70][O:71][C:72](=[O:74])[CH3:73])[CH2:66][S:67][C@H:62]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 15017681HCID 15017681, compoundHCID 15624307HCID 15624307, compound

Product 1

HCID 15017682HCID 15017682, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (Z)-2-(tritylaminothiazol-4-yl)-2-acetoxyiminoacetic acid (1.95 g, 4.0 mmol) and 1-hydroxybenzotriazole (600 mg, 4.0 mmol) in THF (14 ml) was added DCC (824 mg, 4.0 mmol) and the mixture was stirred for 1 hr in an ice bath. Diphenylmethyl 7-amino-3-[(Z)-3-acetoxy-1-propenyl]-3-cephem-4-carboxylate (1.30 g, 2.8 mmol) was added to the suspension and the mixture was stirred for 4 hrs at ambient temperature, filterd, and diluted with AcOEt (60 ml). The organic phase was washed with water, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel (Wakogel C200, 80 g), which was eluted with toluene-AcOEt (6:1). Fractions which contained the product were combined and concentrated in vacuo to give 2.01 g (77%) of diphenylmethyl 7-[(Z)-2-(tritylaminothiazol-4-yl)-2-acetoxyiminoacetamido]-3-[(Z)-3-acetoxy-1-propenyl)-3-cephem-4-carboxylate.

Workup

  1. stirringthe mixture was stirred for 4 hrs at ambient temperature
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a column of silica gel (Wakogel C200, 80 g), which
  6. washwas eluted with toluene-AcOEt (6:1)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-156316d98994492fbd859fc91f545535
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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