Acetyl chloride → HCID 118194694, compound

HRID 1770382Notes

Reaction equation

HRID 1770382 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:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[C:33]([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:35])[CH3:34]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 118194693HCID 118194693, compound

Product 1

HCID 118194694HCID 118194694, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-N-((3S,7S,8S,9S)-8-isopentyl-9-methyl-2-oxo-7-propoxyoxonan-3-yl)-4-methoxypicolinamide (75 mg, 0.166 mmol) were added TEA (34.8 μL, 0.250 mmol) and acetyl chloride (17.8 μL, 0.250 mmol) in DCM (0.832 mL). The reaction was stirred at room temperature for 4 h and then 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 (74 mg, 0.150 mmol, 90%) as a white powder (hygroscopic): IR (thin film): 3383, 2953, 2871, 1772, 1737, 1678, 1506, 1197, 1173 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J=8.2 Hz, 1H), 8.33 (d, J=5.4 Hz, 1H), 7.00 (d, J=5.4 Hz, 1H), 4.74 (dq, J=9.9, 6.3 Hz, 1H), 4.65-4.53 (m, 1H), 3.90 (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), 2.43-2.30 (m, 4H), 2.22-2.07 (m, 1H), 1.96-1.84 (m, 1H), 1.83-1.69 (m, 1H), 1.68-0.98 (m, 12H), 0.96-0.84 (m, 10H); HRMS-ESI m/z [M+H]+ calcd for: C26H41N2O7, 493.2908; found 493.2936.

Workup

  1. additiontreated with Celite® (3 scoopula tip-fulls)
  2. customThe solvent was removed under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-dd98195152c54ff886bea282a7f3d475
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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