Dicyclohexylcarbodiimide → HCID 131712713, compound

HRID 1065196Notes

Reaction equation

HRID 1065196 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33][S:34][C:35]#[N:36])[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.I.N1C=CC=CC=1.[C:44]([O:47][CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:72]([NH2:73])[C:71](=[O:74])[N:53]2[C:54]=1[C:55]([O:57][CH:58]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])(=[O:46])[CH3:45].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:44]([O:47][CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:72]([NH:73][C:27](=[O:28])[C:26]([C:24]3[N:25]=[C:21]([NH:20][C:1]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[S:22][CH:23]=3)=[N:30][O:31][CH2:32][CH2:33][S:34][C:35]#[N:36])[C:71](=[O:74])[N:53]2[C:54]=1[C:55]([O:57][CH:58]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 31273118820-83-2HCID 12884459HCID 12884459, compoundHCID 54174508HCID 54174508, compound

Product 1

HCID 131712713HCID 131712713, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
16 °C

Procedure

A mixture of 1.69 g of the product of Step A, 0.685 g of pyridine hydroiodide, 1.16 g of benzhydryl 3-acetoxymethyl-7-amino-ceph-3-eme-4-carboxylate and 1.36 g of dicyclohexylcarbodiimide was admixed with 17 ml of dimethylformamide and the mixture was cooled to 16° C. for 30 minutes and was then vacuum filtered. 400 ml of ether were added to the filtrate and the mixture was stirred for 5 minutes and allowed to stand for one hour. The mixture was decanted and the gum was washed with ether and was added to 50 ml of ether. The mixture was kneaded until concretization and was vacuum filtered. The product was washed with ether and dried to obtain 1.92 of raw product which was chromatographed over silica gel. Elution with a 91-9 chloroform-acetonitrile mixture yielded 790 mg of amorphous syn isomer of benzhydryl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-thiocyanatoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

Workup

  1. filtrationvacuum filtered
  2. addition400 ml of ether were added to the filtrate
  3. waitto stand for one hour
  4. customThe mixture was decanted
  5. washthe gum was washed with ether
  6. additionwas added to 50 ml of ether
  7. filtrationfiltered
  8. washThe product was washed with ether
  9. customdried
  10. customto obtain 1.92 of raw product which
  11. customwas chromatographed over silica gel
  12. washElution with a 91-9 chloroform-acetonitrile mixture

Sources & evidence

ORD record
ord-b122df6a29ac40df8fffce779d280384
Source dataset
uspto-grants-1982_05
Patent number
US04328225

Reaction notes

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