NADP nicotinamide-adenine-dinucleotide phosphate → (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one

HRID 1052890Notes

Reaction equation

HRID 1052890 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[F:69][C:70]1[CH:75]=[CH:74][C:73]([C:76](=[O:88])[CH2:77][CH2:78][CH2:79][C:80]([N:82]2[CH2:87][CH2:86][O:85][CH2:84][CH2:83]2)=[O:81])=[CH:72][CH:71]=1>CO.C(OCC)(=O)C>[F:69][C:70]1[CH:75]=[CH:74][C:73]([C@@H:76]([OH:88])[CH2:77][CH2:78][CH2:79][C:80]([N:82]2[CH2:83][CH2:84][O:85][CH2:86][CH2:87]2)=[O:81])=[CH:72][CH:71]=1

Participants

7

Reactant 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 62657Potassium Phosphate, TribasicHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 580708091-(4-Fluorophenyl)-5-(morpholin-4-yl)pentane-1,5-dione

Product 1

HCID 23636213(S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
31 °C

Procedure

ES-KRED-106 (5 mg, Chiral Vision) was dissolved in 5 ml buffer (containing 250 mM potassium phosphate, 5 mg NADP+, 330 mM D-glucose, 2 U/ml glucose dehydrogenase, (GDH) pH 7.0). A solution of 1-(4-Fluoro-phenyl)-5-morpholin-4-yl-pentane-1,5-dione in MeOH (4 mg in 0.2 ml) was added. The mixture was stirred at 31° C. for 24 hrs and monitored by HPLC. Ethyl acetate (5 ml) was added and the phases were separated. The organic layer was evaporated to get the (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one. (ee: 90-95%).

Workup

  1. customthe phases were separated
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-65bb7e3e7a1243c9a9a23e083dd22c9d
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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