Potassium Carbonate → HCID 86717768, compound

HRID 513361Notes

Reaction equation

HRID 513361 reaction equation
I[C:2]([I:5])([CH3:4])C.[C:6](=O)([O-])[O-].[K+].[K+].[Si:12]([O:19][C@@H:20]1[N:26]([C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[C:25]2[CH:33]=[C:34]([OH:39])[C:35]([O:37][CH3:38])=[CH:36][C:24]=2[C:23](=[O:40])[N:22]2[CH:41]=[C:42](/[CH:44]=[CH:45]/[CH3:46])[CH2:43][C@@H:21]12)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CC(C)=O>[Si:12]([O:19][C@@H:20]1[N:26]([C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[C:25]2[CH:33]=[C:34]([O:39][CH2:6][CH2:4][CH2:2][I:5])[C:35]([O:37][CH3:38])=[CH:36][C:24]=2[C:23](=[O:40])[N:22]2[CH:41]=[C:42](/[CH:44]=[CH:45]/[CH3:46])[CH2:43][C@@H:21]12)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11483316Propane, 2,2-diiodo-HCID 86717766(11S,11aS)-allyl 11-(tert-butyldimethylsilyloxy)-8-hydroxy-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-11,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate

Product 1

HCID 86717768HCID 86717768, compoundYield 553.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Diiodopropane (0.295 g, 1.00 mmol, 5.0 eq) and potassium carbonate (0.028 g, 0.20 mmol, 1.0 eq) were added to a solution of the phenol 12 (0.100 g, 0.020 mmol, 1.0 eq) in dry acetone (5 mL). The reaction mixture was heated at 60° C. for 6 hours when LC/MS showed complete reaction. The reaction mixture was concentrated to dryness under reduced pressure and the residue was purified by flash chromatography (silica gel, 75/25 v/v n-hexane/EtOAc to 50/50 v/v n-hexane/EtOAc) to afford the product as a colourless oil (0.074 g, 56%). LC/MS (3.853 min (ES+)), m/z: 669.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.26 (s, 1H), 6.90 (s, 1H), 6.68 (s, 1H), 6.24 (d, 1H, J=15.3 Hz), 5.87 (d, 1H, J=8.9 Hz), 5.78 (m, 1H), 5.53 (m, 1H), 5.12 (m, 2H), 4.65 (m, 2H), 4.41 (m, 1H), 4.11 (m, 1H), 3.93 (s, 3H), 3.81 (m, 1H), 3.40 (t, 2H, J=6.7 Hz), 3.05 (dd, 1H, J=16.3, 10.1 Hz), 2.57 (m, 1H), 2.34 (m, 2H), 1.84 (d, 3H, J=6.6 Hz), 0.92 (s, 9H), 0.28 (s, 3H), 0.26 (s, 3H).

Workup

  1. customreaction
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customthe residue was purified by flash chromatography (silica gel, 75/25 v/v n-hexane/EtOAc to 50/50 v/v n-hexane/EtOAc)

Sources & evidence

ORD record
ord-be5e66be8bcc497fb242bb94746ae785
Source dataset
uspto-grants-2015_08
Patent number
US09102704B2

Reaction notes

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