Triphenylphosphine → HCID 57190401, compound

HRID 864273Notes

Reaction equation

HRID 864273 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]1[C:38]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[N:37][CH:36]=[C:35]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)[N:34]=1.[CH2:54]([C@@H:59]1[O:61][C@H:60]1[CH2:62]O)[CH2:55][CH2:56][CH2:57][CH3:58]>C(Cl)(Cl)Cl>[F:32][C:33]1[C:38]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[N:37][CH:36]=[C:35]([C:47]2[CH:48]=[CH:49][C:50]([O:53][CH2:62][C@H:60]3[C@H:59]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[O:61]3)=[CH:51][CH:52]=2)[N:34]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10888033HCID 10888033, compoundHCID 1355744622-Fluoro-3-octyl-6-(4-hydroxyphenyl)pyrazine

Product 1

HCID 57190401HCID 57190401, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In an analogous reaction to Example 5a, 3.04 g (11.60 mmol) of triphenylphosphine, 1.82 ml (11.60 mmol) of diethyl azodicarboxylate, 2.00 g (7.00 mmol) of 2-fluoro-3-octyl-6-(4-hydroxyphenyl)pyrazine and 1.67 g (11.60 mmol) of (2S,3S)-3-pentyloxiran-2-ylmethanol give 1.20 g of [(2S,3S)-3-pentyloxiran-2-yl]methyl 4-(2-fluoro-3-octylpyrazin-6-yl)phenyl ether of [α]D20 (c = 0,995 in CHCl3)=-16.58. ##STR28##

Sources & evidence

ORD record
ord-a3cce9cabc3d4457a97d073cc4af0184
Source dataset
uspto-grants-1996_10
Patent number
US05562859

Reaction notes

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