Dicyclohexylcarbodiimide → HCID 54213439, compound

HRID 439878Notes

Reaction equation

HRID 439878 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([N:8]([OH:12])[C:9]([NH2:11])=[O:10])[CH3:7])=[CH:2]1.[CH3:13][C@H:14]([C:27](O)=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:26][O:25][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[CH:24]=[C:15]([C@H:14]([CH3:13])[C:27]([O:12][N:8]([CH:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH3:7])[C:9]([NH2:11])=[O:10])=[O:28])[CH:16]=[CH:17]2

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130007N-1-(fur-3-ylethyl)-N-hydroxyureaHCID 156391Naproxen

Product 1

HCID 54213439HCID 54213439, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-1-(fur-3-yl)ethyl-N-hydroxyurea (1.00 g, 5.9 mmol), prepared as described in U.S. Pat. No. 5,112,848, in CH2Cl2 (25 mL) was added naproxen (135 g, 5.9 mmol) followed by dicyclohexylcarbodiimide (1.34 g, 6.49 mmol), and a crystal of 4-N,N-dimethylaminopyridine. The reaction was stirred for 18 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (ether), followed by crystallization in ethyl acetate/hexanes to give N-[(S)-2-(6-methoxynaphth-2-yl)propionyloxy]-N-[1-(fur-3-yl)ethyl]urea (1.54 g). m.p. 128.5°-134° C. 1H NMR (300 MHz, DMSO-d6, mixture of diastereomers) δ 0.72 and 1.12 (bm, 3H), 1.48 (bm, 3H), 3.87 (s, 3H), 4.13 (bm, 1H), 5.14 (bm, 1H), 6.79 and 6.94 (bs, 2H), 7.16 (m, 2H), 7.29-7.46 (m, 3H), 7.69-7.86 (m, 3H). MS (DCI/NH3) m/e 383 (M+H)+. Analysis calc'd for C21H22N2O5 : C, 65.95; H, 5.80; N, 7.33. Found: C, 65.39; H; 5.80; N, 7.26.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (ether)
  4. customfollowed by crystallization in ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bd02401f04754aee997b55f1a6417696
Source dataset
uspto-grants-1996_05
Patent number
US05516789

Reaction notes

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