Pyridine → HCID 86701277, compound

HRID 2276077Notes

Reaction equation

HRID 2276077 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:10][C@@H:11]1[C@@H:19]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:18](=[O:27])[O:17][CH2:16][C@H:15]([NH:28][C:29](=[O:39])[C:30]2[C:35]([OH:36])=[C:34]([O:37][CH3:38])[CH:33]=[CH:32][N:31]=2)[C:14](=[O:40])[O:13][C@H:12]1[CH3:41])(=[O:9])[CH:6]([CH3:8])[CH3:7].N1C=CC=CC=1>C(Cl)Cl>[C:5]([O:10][C@@H:11]1[C@@H:19]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:18](=[O:27])[O:17][CH2:16][C@H:15]([NH:28][C:29](=[O:39])[C:30]2[C:35]([O:36][C:1](=[O:3])[CH3:2])=[C:34]([O:37][CH3:38])[CH:33]=[CH:32][N:31]=2)[C:14](=[O:40])[O:13][C@H:12]1[CH3:41])(=[O:9])[CH:6]([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86701278HCID 86701278, compound

Product 1

HCID 86701277HCID 86701277, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Acetyl chloride (9 μL, 0.125 mmol) was added to a solution of (3S,6S,7R,8R)-8-(cyclohexylmethyl)-3-(3-hydroxy-4-methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (50 mg, 0.100 mmol) and pyridine (40 μL, 0.480 mmol) in CH2Cl2 (1 mL), and the reaction was stirred at ambient temperature (about 22° C.) overnight. The solution was loaded directly onto a pre-packed SiO2 column for purification by column chromatography (0→30% EtOAc/CH2Cl2) to afford the title compound (28 mg, 52%) as a white solid: mp 164-170° C.; 1H NMR (400 MHz, CDCl3) δ 8.70 (d, J=7.5 Hz, 1H), 8.35 (d, J=5.4 Hz, 1H), 7.03 (d, J=5.5 Hz, 1H), 5.47 (br s, 1H), 5.25-5.11 (m, 1H), 5.03 (t, J=9.9 Hz, 1H), 4.97-4.84 (m, 1H), 3.92 (s, 3H), 3.72 (br s, 1H), 2.69 (dd, J=16.8, 7.0 Hz, 1H), 2.60 (sept, J=14.0, 7.0 Hz, 1H), 2.40 (s, 3H), 1.83-1.54 (m, 6H), 1.36-1.02 (m, 14H), 0.94-0.67 (m, 2H); HRMS-ESI (m/z): calcd for C28H38N2O10, 562.2526; found, 562.2516.

Workup

  1. customThe solution was loaded directly onto a pre-packed SiO2 column for purification by column chromatography (0→30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-e7abe172a49f47ee9dbac9811b48fd8a
Source dataset
uspto-grants-2015_09
Patent number
US09131690B2

Reaction notes

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