Dimethyl Sulfoxide → HCID 58691210, compound

HRID 1392084Notes

Reaction equation

HRID 1392084 reaction equation
[CH:1]1([CH2:4][N:5]([CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH2:25])[C:6](=[O:22])[CH:7]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:8]C=C)[CH2:3][CH2:2]1.CS(C)=O>C1(C)C=CC=CC=1.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH:1]1([CH2:4][N:5]2[CH:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:24]=[CH:25][CH2:8][CH:7]([N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[C:6]2=[O:22])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 58691201N-(cyclopropylmethyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(1-phenylprop-2-en-1-yl)pent-4-enamide

Product 1

HCID 58691210HCID 58691210, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (N-(cyclopropylmethyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(1-phenylprop-2-en-1-yl)pent-4-enamide (4c) (210 mg) dissolved in Toluene (25 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (21 mg) and the reaction mixture was stirred at 80° C. for 1 h, then cooled to RT. DMSO (0.1 mL) was added to the reaction mixture which was stirred for 2 h, then concentrated. The crude product was directly purified via flash chromatography (gradient—5%, 10% and 15% EtOAc/hexanes) to give a diastereomeric mixture (1.5:1) of the title compound (128 mg, 66%). 1H NMR (300 MHz, CDCl3) δ 0.03-0.09 (m, 1H), 0.22-0.34 (m, 2H), 0.46-0.57 (m, 1H), 0.66-0.72 (m, 0.6H), 1.03-1.09 (m, 0.4H), 2.42-2.48 (m, 1H), 2.98 (dd, 0.6H), 3.20 (dd, 0.4H), 3.55 (dd, 0.6H), 3.61-3.74 (m, 1H), 3.94 (dd, 0.4H), 5.09 (dd, 0.4H), 5.28 (bd, 0.4H), 5.57 (dd, 0.6H), 5.77(d, 0.6H), 6.00-6.08 (m, 1H), 6.26-6.35 (m, 1H), 7.35-7.48 (m, 5H), 7.65-7.88 (m, 4H). MS APCI, m/z=387 (M+1). LC/MS 2.66 min., Method A.

Workup

  1. temperaturecooled to RT
  2. stirringwas stirred for 2 h
  3. concentrationconcentrated
  4. customThe crude product was directly purified via flash chromatography (gradient—5%, 10% and 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0fc153da371741d58bf370003b62c82f
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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