Potassium Carbonate → HCID 118194671, compound

HRID 1770381Notes

Reaction equation

HRID 1770381 reaction equation
[OH:1][C:2]1[C:3]([C:10]([NH:12][C@H:13]2[CH2:21][CH2:20][CH2:19][C@H:18]([O:22][CH2:23][CH2:24][CH3:25])[C@@H:17]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C@H:16]([CH3:31])[O:15][C:14]2=[O:32])=[O:11])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([O-])([O-])=O.[K+].[K+].[C:39]([O:42][CH2:43]Br)(=[O:41])[CH3:40]>CC(C)=O.C(Cl)Cl>[C:39]([O:42][CH2:43][O:1][C:2]1[C:3]([C:10](=[O:11])[NH:12][C@H:13]2[CH2:21][CH2:20][CH2:19][C@H:18]([O:22][CH2:23][CH2:24][CH3:25])[C@@H:17]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C@H:16]([CH3:31])[O:15][C:14]2=[O:32])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9])(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68536Bromomethyl acetateHCID 118194693HCID 118194693, compound

Product 1

HCID 118194671HCID 118194671, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydroxy-N-((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)-4-methoxypicolinamide (125 mg, 0.277 mmol) and K2CO3 (77 mg, 0.555 mmol) in acetone (2.77 mL) was added bromomethyl acetate (54.4 μL, 0.555 mmol). The reaction was sealed, heated to 50° C., stirred at this temperature for 6 h, and then cooled to room temperature. The mixture was diluted with DCM (4 mL) and treated with Celite® (3 scoopula tip-fulls). The solvent was removed under reduced pressure and the resulting adsorbed material was directly loaded onto a column and purified using flash column chromatography (24 g SiO2, 0→100% EtOAc/hexanes) to afford the title compound (112 mg, 0.214 mmol, 77%) as a sticky, slightly yellow oil: IR (thin film): 3378, 2954, 2872, 1740, 1677, 1504, 1202 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=8.1 Hz, 1H), 8.28 (d, J=5.4 Hz, 1H), 6.95 (d, J=5.4 Hz, 1H), 5.74 (s, 2H), 4.74 (dq, J=10.1, 6.3 Hz, 1H), 4.61 (app dt, J=10.7, 7.6 Hz, 1H), 3.91 (s, 3H), 3.52 (app dt, J=8.9, 6.4 Hz, 1H), 3.31-3.22 (m, 1H), 3.15 (app dt, J=8.9, 6.6 Hz, 1H), 2.45-2.33 (m, 1H), 2.21-2.09 (m, 1H), 2.07 (s, 3H), 1.98-1.86 (m, 1H), 1.85-1.70 (m, 1H), 1.67-1.28 (m, 10H), 1.24-1.03 (m, 2H), 0.97-0.84 (m, 10H); HRMS-ESI m/z [M+Na]1 calcd for: C27H42N2NaO8, 545.2833; found, 545.2853.

Workup

  1. customThe reaction was sealed
  2. temperaturecooled to room temperature
  3. additiontreated with Celite® (3 scoopula tip-fulls)
  4. customThe solvent was removed under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-babde80ea01543979da8f9c01dfbb75f
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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