Dicyclohexylcarbodiimide → HCID 12769261, compound

HRID 1706835Notes

Reaction equation

HRID 1706835 reaction equation
[C:1]1(/[C:7](=[N:11]/[O:12][C:13]([C:16]([NH:18][C:19]([NH2:21])=[O:20])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22]1(N=C=NC2CCCCC2)CCCCC1.C[CH:38]([S:65][C:66]1[NH:70][N:69]=[N:68][N:67]=1)[C:39]1[CH2:40][S:41][C@@H:42]2[C@H:62]([NH2:63])[C:61](=[O:64])[N:43]2[C:44]=1[C:45]([O:47][CH:48]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]>ClCCl.CN(C)C=O>[CH3:22][N:70]1[C:66]([S:65][CH2:38][C:39]2[CH2:40][S:41][C@@H:42]3[C@H:62]([NH:63][C:8](=[O:10])/[C:7](/[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11]\[O:12][C:13]([C:16]([NH:18][C:19]([NH2:21])=[O:20])=[O:17])([CH3:15])[CH3:14])[C:61](=[O:64])[N:43]3[C:44]=2[C:45]([O:47][CH:48]([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[O:46])=[N:67][N:68]=[N:69]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12769264HCID 12769264, compoundHCID 178477368HCID 178477368, compound

Product 1

HCID 12769261HCID 12769261, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Z-2-phenyl-2-(2-ureidocarbonylprop-2-yloxyimino)acetic acid (460 mg) in dichloromethane (6 ml) and dimethylformamide (2 ml) was added slowly to a stirred solution of dicyclohexylcarbodiimide (370 mg) and diphenylmethyl (6R,7R)-3-(1-methyltetrazol-5-ylthiomethyl)-7-aminoceph-3-em-4-carboxylate (790 mg) in dichloromethane (10 ml) and dimethylformamide (3 ml) and the mixture was stirred for 20 hr. The solution was filtered, the filtrate was evaporated, and the residue was dissolved in ethyl acetate (50 ml). The filtered solution was washed with 2N- hydrochloric acid (2×15 ml) and saturated sodium hydrogen carbonate solution (2×15 ml), dried (Na2SO4) and evaporated. The residue was purified on silica gel plates in light petroleum-ethyl acetate (1:1 v/v) to give the ester, 580 mg, λmax (Nujol) 3400, 3280 (NH, NH2), 1788 (β-lactam), 1720, 1710 (--CO2R), 1685, 1670 cm-1 (--CONHCONH2, --CONH--), τ(DMSO d6) 0.60 (--CONHCO--), 8.59 (--C(Me)2 --), 2.0-2.9 (Phenyls), --0.06 (--CONH--), 3.87 (7 H), 4.62 (6H), 5.9, 6.5 (2--CH2 --), 5.59, 5.79 (3--CH2 --), 6.09 (--N--Me), 3.0 (--CH Ph2).

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  4. washThe filtered solution was washed with 2N- hydrochloric acid (2×15 ml) and saturated sodium hydrogen carbonate solution (2×15 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified on silica gel plates in light petroleum-ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-ec3422eae4ca4c08910c963b22237073
Source dataset
uspto-grants-1980_06
Patent number
US04208517

Reaction notes

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