Pyridine → HCID 57794772, compound

HRID 2099266Notes

Reaction equation

[OH:1][C@@H:2]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6].N1C=CC=CC=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:1][C@@H:2]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH:4]([C:5]#[N:6])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(4R)-4-hydroxy-2-phenyl-5-[(phenylmethyl)oxy]pentanenitrile (16.0 g, 57 mmol), accessed via the method of preparation 1, was dissolved in 116 mL CHCl3 and 116 mL Pyridine (25 eq) with DMAP (0.70 g, 5.7 mmol, 0.1 eq) and cooled to 0° C. 4-methylbenzenesulfonyl chloride (43.5 g, 228 mmol, 4 eq) was added to the reaction mixture and stirred 3 days at 0° C. The reaction mixture was washed successively with 1N HCl (4×250 mL) and brine, dried over MgSO4, filtered and concentrated to a red oil. The crude material was purified by flash chromatography (SiO2, 10→25% EtOAc/Hexanes) to give the diastereomeric product as a yellow oil (14.88 g, 34.2 mmol, 60%). ES-LCMS m/z 458.36 (M+Na).

Workup

washThe reaction mixture was washed successively with 1N HCl (4×250 mL) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to a red oil
customThe crude material was purified by flash chromatography (SiO2, 10→25% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-5064a56a48e74ee093060b5c54fb0c6b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569579B2

Reaction notes

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