Potassium Carbonate → HCID 69627441, compound

HRID 1281394Notes

Reaction equation

HRID 1281394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14](=[O:36])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:35])[NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH:11]=[C:10]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=3)[C:9]=2[OH:44])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:52][C:53]([O:55][CH3:56])=[O:54]>CN(C=O)C>[CH3:56][O:55][C:53](=[O:54])[CH2:52][O:44][C:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:13][C:12]([C:14](=[O:36])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:35])[NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 18425917HCID 18425917, compound

Product 1

HCID 69627441HCID 69627441, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,3″-dichloro-5′-[6-(naphthalen-1-ylcarbamoyloxy)-hexylcarbamoyl]-[1,1′;3′1″]-terphenyl-2′-ol (0.320 g, 0.510 mmol) and K2CO3 (0.078 g, 0.561 mmol) in DMF (10 mL) at room temperature was added dropwise methyl bromoacetate (0.097 mL, 1.02 mmol). After 18 h at this temperature, it was concentrated and then diluted with excess EtOAc (250 mL). The organic layer was washed with 1 N HCl (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL) and then dried (MgSO4). After concentration, the residue was purified by flash chromatography (30 to 50% EtOAc/petroleum ether gradient) to afford the product (0.231 g, 65%) as a solid; 1H NMR (DMSO-d6) δ 1.32-1.49 (m, 4H), 1.49-1.73 (m, 4H), 3.23-3.35 (m, 2H), 3.44 (s, 3H), 3.99 (s, 2H), 4.11 (t, J=6.3 Hz, 2H), 7.45-7.63 (m, 10H), 7.69 (s, 2H), 7.73 (d, J=9.4 Hz, 1H), 7.87-7.94 (m, 3H), 8.02-8.12 (m, 1H), 8.61 (t, J=5.5 Hz, 1H), 9.49 (s, 1H); mass spectrum [(+) ESI], m/z 700 (M+H)+.

Workup

  1. concentrationAfter 18 h at this temperature, it was concentrated
  2. additiondiluted with excess EtOAc (250 mL)
  3. washThe organic layer was washed with 1 N HCl (25 mL), sat. aq. NaHCO3 (25 mL), and brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography (30 to 50% EtOAc/petroleum ether gradient)

Sources & evidence

ORD record
ord-4096b74ce9e84c4fbd163604ab61223c
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

Loading…