Benzyl lactate → HCID 19006656, compound

HRID 1742562Notes

Reaction equation

HRID 1742562 reaction equation
[C:1](OCC1C=CC=CC=1)(=O)[CH:2]([CH3:4])O.[N:14](C(OCC)=O)=NC(OCC)=O.[CH2:26]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[N:46]=[CH:45][C:44]([OH:47])=[CH:43][N:42]=2)=[C:37]([F:48])[CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>>[CH2:26]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[N:46]=[CH:45][C:44]([O:47][CH:2]([C:1]#[N:14])[CH3:4])=[CH:43][N:42]=2)=[C:37]([F:48])[CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 98054Benzyl lactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19006677HCID 19006677, compound

Product 1

HCID 19006656HCID 19006656, compound

Procedure

Optically active benzyl lactate is etherified by means of diethyl azodicarboxylate (DEAD)/triphenylphosphine with 2-(4-octyloxy-2-fluorophenyl)-5-hydroxypyrimidine (prepared in accordance with Example 1) and the benzyl group is then split off hydrogenolytically. The acid so obtained is converted as usual into the nitrile (oxalyl chloride, ammonia, thionyl chloride). Optically active 2-(4-octyloxy-2-fluorophenyl)-5-(1-cyanoethoxy)-pyrimidine is obtained.

Workup

  1. customthe benzyl group is then split off hydrogenolytically
  2. customThe acid so obtained

Sources & evidence

ORD record
ord-986e24c218414a97946534b041793189
Source dataset
uspto-grants-1994_08
Patent number
US05340497

Reaction notes

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