Pyridine → HCID 86628905, compound

HRID 1919431Notes

Reaction equation

HRID 1919431 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:25])([CH3:24])[C@@H:11]([OH:23])[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6].[CH3:26][CH:27]([CH3:31])[C:28](Cl)=[O:29].N1C=CC=CC=1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:24])([CH3:25])[C@@H:11]([O:23][C:28](=[O:29])[CH:27]([CH3:31])[CH3:26])[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 86628904HCID 86628904, compound

Product 1

HCID 86628905HCID 86628905, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-hydroxy-3,3-dimethylbutanoate (36b) (0.2 g, 0.49 mmol) was reacted with 0.16 mL (0.16 g, 1.5 mmol) of 2-methylpropanoyl chloride in 5 mL of anhydrous dichloromethane (DCM) in the presence of 0.11 mL (0.11 g, 1.3 mmol) of pyridine. After work-up and isolation, the crude material was purified by silica gel column chromatography using ethyl acetate (EtOAc) and hexane (Hxn) mixtures (EtOAc/Hxn=1:2) as eluent to provide 0.23 g (99% yield) of the title compound (36c) as a colorless oil. Rf=0.55 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.12-1.15 (2s, 3H), 1.21-1.26 (m, 12H), 1.50-1.58 (2d, J=5.2, 5.6 Hz, 3H), 2.30-2.36 (m, 2H), 2.64-2.71 (m, 1H), 3.31-3.36 (m, 2H), 3.69-3.72 (m, 2H), 3.99-4.02 (2d, J=9.2, 9.6 Hz, 1H), 4.16 (d, J=9.6 Hz, 1H), 4.21-4.28 (m, 2H), 4.75-4.79 (2s, 1H), 6.77-6.82 (m, 1H) ppm. MS (ESI) m/z: 496.99 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up and isolation, the crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d0ceadaca53341b8802251689b17018d
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

Loading…