Phosphate → (-)-2-[4-(3-Hydroxy-1-butyl)-phenyl]-5-hydroxy-pyridine

HRID 1728278Notes

Reaction equation

HRID 1728278 reaction equation
[C:1]([O:4][CH:5]([CH3:25])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][Si](C)(C)C)=[CH:16][N:15]=2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].P([O-])([O-])([O-])=[O:27]>C(Cl)(Cl)Cl>[OH:4][CH:5]([CH3:25])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][N:15]=2)=[CH:12][CH:13]=1.[C:1]([O:4][CH:5]([CH3:25])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([OH:27])[CH:19]=[CH:18][CH:17]=[CH:16][NH:15]2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 190172512-[4-(3-Acetoxy-1-butyl)phenyl]-5-trimethylsilyloxy-pyridine

Product 2

HCID 19017166(-)-2-[4-(3-Hydroxy-1-butyl)-phenyl]-5-hydroxy-pyridineHCID 67824305(-)-2-[4-(3-Acetoxy-1-butyl)phenyl]-2-hydroxy-pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

12 g of 2-[4-(3-acetoxy-1-butyl)phenyl]-5-trimethylsilyloxy-pyridine, 300 ml of 0.3M phosphate buffer solution (pH 7.0), 30 ml of chloroform and 3.0 g of lipase (genus Arthobacter) are reacted to give 4.5 g of (-)-2-[4-(3-hydroxy-1-butyl)-phenyl]-5-hydroxy-pyridine and 4.2 g of (-)-2-[4-(3-acetoxy-1-butyl)phenyl]-2-hydroxy-pyridine.

Sources & evidence

ORD record
ord-0c33416f645e4e9eb7ff733f7d23ab2c
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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