Phosphate → Ethyl (2R)-2-fluorooctanoate

HRID 1603315Notes

Reaction equation

HRID 1603315 reaction equation
[F:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4].P([O-])([O-])([O-])=O.F[C@@H](CCCCCC)C(OCC)=O.[OH-].[Na+]>O>[F:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 14798Sodium HydroxideHCID 11789996Ethyl 2-fluorooctanoateHCID 54108055ethyl (S)-(-)-2-fluorooctanoate

Product 1

HCID 54108054Ethyl (2R)-2-fluorooctanoateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

--Quantities: partially resolved ethyl 2-fluorooctanoate 68 (44 g, 0.23 mol), 0.063M phosphate buffer (pH 7.0) (400 ml), deionised water (400 ml), Pseudomonas lipase (Amano PS) (40 mg). The experimental procedure was as described for compound 66. The hydrolysis was continued until the rate of reaction was almost zero, as indicated by a constant pH with zero addition of alkali (reaction time 5 h, 38 ml of 1M sodium hydroxide solution added i.e. 16% hydrolysis). The mixture was extracted with ether (3 times) and the combined organic solutions were washed with brine, dried (K2CO3) and evaporated. The liquid was distilled to give ethyl (R)-(+)-2-fluoroacetate 69 (30.7 g, 0.23 mol), b.p. 63° C. at 0.6 mm Hg; [α]D26 =+8.5° (c 5.9 in CHCl3).

Workup

  1. customThe hydrolysis was continued until the rate of reaction
  2. extractionThe mixture was extracted with ether (3 times)
  3. washthe combined organic solutions were washed with brine
  4. dry with materialdried (K2CO3)
  5. customevaporated
  6. distillationThe liquid was distilled

Sources & evidence

ORD record
ord-71f00e6254e840ed86c231173739378d
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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