Dicyclohexylcarbodiimide → HCID 86653385, compound

HRID 1192772Notes

Reaction equation

HRID 1192772 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5](/[CH:10]=[CH:11]/[C:12]([CH2:14][C:15](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:24]([O:25][CH3:26])[C:22]([OH:23])=[CH:21][CH:20]=2)=[O:16])=[O:13])[CH:4]=1.[C:28](O)(=[O:48])/[CH:29]=[CH:30]\[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.O>[C:28]([O:9][C:8]1[CH:7]=[CH:6][C:5]([CH:10]=[CH:11][C:12](=[O:13])[CH2:14][C:15](=[O:16])[CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][C:22]([OH:23])=[C:24]([O:25][CH3:26])[CH:27]=2)=[CH:4][C:3]=1[O:2][CH3:1])(=[O:48])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 969516CurcuminHCID 86653383HCID 86653383, compound

Product 1

HCID 86653385HCID 86653385, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of curcumin (300 mg, 0.81 mmol), cis-eicosapentaenoic acid (250 mg, 0.83 mmol) and catalytic amount of 4-(dimethylamino)pyridine in dichloromethane (10 mL) was added a solution of N,N′-dicyclohexylcarbodiimide (252 mg, 1.2 mmol) in dichloromethane (5 mL) for 5 min at ice cold temperature. The mixture was stirred at rt for 16 h and diluted with water. The dichloromethane layer was separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined dichloromethane layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10) mixture as an eluent to give the product as an oil (235 mg, 44%). IR (neat) νmax 3013, 2961, 2929, 1762, 1630, 1593, 1268, 1123, 1032, 970 cm−1; 1H NMR (CDCl3) δ 7.61 (1H, d, J=16.0 Hz, H-1), 7.60 (1H, d, J=15.6 Hz, H-7), 7.03-7.16 (5H, m, H-2′, 2″, 5′, 6′, 6″), 6.93 (1H, d, J=8.4 Hz, H-5″), 6.55 (1H, d, J=16 Hz, H-2), 6.49 (1H, d, J=16 Hz, H-6), 5.89 (1H, br s, Ar—OH), 5.83 (1H, s, H-4), 5.38-5.39 (10H, m, H-5′″, 6′″, 8′″, 9′″, 11′″, 12′″, 14′″, 15′″, 17′″, 18′″), 3.95 (3H, s, Ar—OCH3), 3.87 (3H, s, Ar—OCH3), 2.84-2.86 (8H, m, H-7′″, 10′″, 13′″, 16′″), 2.58-2.66 (2H, m, H-2′″), 2.22-2.23 (2H, m, H-19′″), 2.05-2.09 (2H, m, H-4′″), 1.82-187 (2H, m, H-3′″), 0.97 (3H, t, J=7.4 Hz, H-20′″); LCMS (ESI, negative ion mode): m/z 651 (M-H)−.

Workup

  1. customThe dichloromethane layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×100 mL)
  3. washThe combined dichloromethane layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-ae2674d862ca4b4287d5d91a38e3330a
Source dataset
uspto-grants-2014_03
Patent number
US08680143B2

Reaction notes

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