2-Chloro-5-fluoro-1,3-benzoxazole → HCID 12096142, compound

HRID 1635650Notes

Reaction equation

HRID 1635650 reaction equation
[Cl-].[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][NH2+:8]1)=[O:6])[CH3:3].Cl[C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:17]=2[N:18]=1>>[F:23][C:20]1[CH:21]=[CH:22][C:16]2[O:15][C:14]([N:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]3[C:5]([O:4][CH2:2][CH3:3])=[O:6])=[N:18][C:17]=2[CH:19]=1

Participants

3

Reactant 2

HCID 141698172-Chloro-5-fluoro-1,3-benzoxazoleHCID 86591487HCID 86591487, compound

Product 1

HCID 12096142HCID 12096142, compound

Procedure

The title compound was prepared by a similar method to Preparation 2 from (2S)-2-(ethoxycarbonyl)piperidinium chloride [see J. Am. Chem. Soc. (1993), 115, 9925-9938] and 2-chloro-5-fluoro-1,3-benzoxazole [see J. Med. Chem. (1988), 31, 1719-1728]. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 3:1, by volume, hexane:ethyl acetate, to afford ethyl (2S)-1-(5-fluoro-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 3:1, by volume, hexane

Sources & evidence

ORD record
ord-63e65cf0d73b4bc183e6f252425098bb
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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