methyl (S)-3-hydroxyheptanoate → (R)-5-Hexyloxy-2-[4-(3-fluoroheptyloxy)phenyl]pyrimidine

HRID 1197393Notes

Reaction equation

HRID 1197393 reaction equation
CS([O:5][CH2:6][CH2:7][C@H:8]([F:13])[CH2:9][CH2:10][CH2:11][CH3:12])(=O)=O.O[C@@H](CCCC)CC(OC)=O.[CH2:25]([O:31][C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](O)=[C:40](F)[CH:39]=2)=[N:36][CH:37]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>>[CH2:25]([O:31][C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41]([O:5][CH2:6][CH2:7][C@H:8]([F:13])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:40][CH:39]=2)=[N:36][CH:37]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 10419468methyl (S)-3-hydroxyheptanoateHCID 22850585HCID 22850585, compoundHCID 1356750155-n-Hexyloxy-2-(4-hydroxy-3-fluorophenyl)pyrimidine

Product 1

HCID 53934372(R)-5-Hexyloxy-2-[4-(3-fluoroheptyloxy)phenyl]pyrimidineYield 48.5%

Procedure

The titled compound was synthesized from (R)-3-fluoroheptyl methanesulfonate, derived from methyl (S)-3-hydroxyheptanoate (98.0% ee, [α]D20 =-8.71°), and 5-n-hexyloxy-2-(4-hydroxy-3-fluorophenyl)pyrimidine.

Sources & evidence

ORD record
ord-c1edb33f48a54609b069763986599c61
Source dataset
uspto-grants-1994_01
Patent number
US05275756

Reaction notes

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