Triphenylphosphine → HCID 57198907, compound

HRID 1780577Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[C:38]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:37][CH:36]=[C:35]([C:48]2[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=2)[N:34]=1.[CH2:55]([C@@H:60]1[O:62][C@H:61]1[CH2:63]O)[CH2:56][CH2:57][CH2:58][CH3:59]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:37][CH:36]=[C:35]([C:48]2[CH:49]=[CH:50][C:51]([O:54][CH2:63][C@H:61]3[C@H:60]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[O:62]3)=[CH:52][CH:53]=2)[N:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.91 g (5.25 mmol) of diethyl azodicarboxylate is added dropwise at 0° C. to 1.37 g (5.25 mmol) of triphenylphosphine in 20 ml of tetrahydrofuran, and the mixture is stirred at 0° C. for 30 minutes. 1.11 g (3.50 mmol) of 2-fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridine (prepared as described in EXAMPLE 21) and 0.75 g (5.25 mmol) of (2S,3S)-3-pentyl-2-oxiranylmethanol are then added. After a reaction time of 18 hours at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate). Recrystallization from hexane gives 0.85 g of (2S,3S)-3-pentyloxiran-2-ylmethyl 4-(2-fluoro-3-octyloxypyridin-6-yl)phenyl ether having an [α]D20 (2.6% in CH2Cl2) of -18.01°. ##STR71##

Workup

distillationAfter a reaction time of 18 hours at room temperature, the solvent is distilled off
customthe residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate)
customRecrystallization from hexane

Sources & evidence

ORD record: ord-fba517eaf113464980a2132e238c22d9
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05630962

Reaction notes

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