Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1730893Notes

Reaction equation

HRID 1730893 reaction equation
N[C@@H]1C(=O)N2C(C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=[O:12])=C(C=C)CS[C@H]12.[CH:29]1([N:35]=[C:36]=[N:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C)C=O>[C:36]([NH:35][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)([NH:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)=[O:12]

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 10960166HCID 10960166, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of diphenylmethyl 7βamino-3-vinylceph-3-em-4-carboxylate (1.57 g., 4 mmole) in methylene dichloride (25 ml.) with dicyclohexylcarbodiimide (907 mg., 4.4 mmole) was treated slowly (over 10 minutes) with a solution of D-2-t-butoxycarbonylamino-2-phenylacetic acid (1.1 g., 4.4 mmole) in N,N-dimethylformamide (10 ml.). The mixture was stirred at 23° for 30 minutes and dicyclohexylurea removed by filtration. The filtrate was washed with water and dried and evaporated in vacuo to give a pale yellow solid. This material was crystallised from methanol, and the isolated material washed with ether, to give the crude title cpompound (2.2 g.) (contaminated with dicyclohexylurea). The crude compound in benzene :ethyl acetate (2:5) was filtered through a short column of Kieselgel 0.02 - 0.5 mm., 10 cm. × 2.5 cm.). Evaporation of the solvent in vacuo and washing the crystalline residue with ether gave the pure title compound (1.6 g., 64%) as small needles m.p. 200°-202°, [α]D - 129° (CHCl3), λmax 294.5 nm. (ε 14,400), νmax. 3395 (NH), 1780 (β-lactam), 1712 (CO2R), 1690 and 1500 (CONH) and 912 cm.-1 (CH=CH2),τ(CDCl3) 3.05 (CHPh2),3.03 (CH=CH2, dd, J 17 and 11 Hz). 3.08 (NH, d, J 9 Hz) 4.23 (C(7) -H, dd, J 9 and 4.5 Hz), 4.28 (CH-NH, d, J 7 Hz), 4.65 and 4.79 (CH=CH2, two d, J 17 and 11 Hz resp.), 4.77 (CH-NH, d, J 7 Hz), 5.10 (C(6) -H, d, J 4.5 Hz), 6.46 and 6.70 (C(2) -CH, AB-q, J 18 Hz) 8.58 (C[CH3 ]3). (Found: C, 66.6; H, 5.6; N, 6.4; S, 5.1. C35H35N3O6S requires C, 67.2; H, 5.65; N, 6.7; S, 5.1%).

Workup

  1. customdicyclohexylurea removed by filtration
  2. washThe filtrate was washed with water
  3. customdried
  4. customevaporated in vacuo
  5. customto give a pale yellow solid
  6. customThis material was crystallised from methanol
  7. washthe isolated material washed with ether

Sources & evidence

ORD record
ord-abcf4c2ebe044a37a004ca5c1f485c42
Source dataset
uspto-grants-1976_11
Patent number
US03994884

Reaction notes

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