Pyridine → HCID 57077212, compound

HRID 1463462Notes

Reaction equation

[C:1]([O:4][CH:5]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]([CH:15]([CH2:20][CH2:21]O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:16]([O:18][CH3:19])=[O:17])[C:6]1=[O:40])(=[O:3])[CH3:2].N1C=CC=CC=1.C1C[O:50]CC1>>[C:1]([O:4][C@@H:5]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]([CH:15]([CH:20]([OH:50])[CH3:21])[C:16]([O:18][CH3:19])=[O:17])[C:6]1=[O:40])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 1049Pyridine

HCID 8028Tetrahydrofuran

HCID 67828884HCID 67828884, compound

Product 1

HCID 57077212HCID 57077212, compound

Procedure

The diastereomeric mixture of Example 2 (444 mg, 0.793 mmol) in anhydrous THF (4 mL) was treated with HF/pyridine (4.4M, 1.80 mL, 7.93 mmol) at room temperature for 5 days. Quench and work up as in the above Example 5, followed by chromatography (40% ethyl acetate/hexane) gave title compound as a white solid. (139 mg, 54%).

Workup

customQuench

Sources & evidence

ORD record: ord-258b7481f1cd468cb940ae2c418da6cb
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05300638

Reaction notes

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