Acetone → 6-(Trifluoroacetamido)hexanoic Acid

HRID 2098249Notes

Reaction equation

HRID 2098249 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12])=[O:4].C(Cl)(Cl)Cl.CC(C)=O>B([O-])([O-])[O-]>[F:1][C:2]([F:15])([F:16])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6212ChloroformHCID 21932549Methyl 6-(2,2,2-trifluoroacetamido)hexanoate

Product 1

HCID 3035936-(Trifluoroacetamido)hexanoic AcidYield 89%

Reagents, catalysts & solvents 1

HCID 26574BorateSolvent

Procedure

Next, after dissolving Methyl 6-trifluoroacetamidohexanoate (3.7 g, 15.4 mmol) in 10 mM of a borate buffer pH8.0 (3000 ml), a porcine liver derived carboxylesterase (2160U, 1.2 ml) was added, and a reaction performed at 30° C. After 72 hours had passed since the start of the reaction, after boiling for 10 minutes at 100° C. and stopping the reaction, the reaction solution was concentrated and applied to a silica gel column chromatography (2.0×30 cm) equilibrated (10 ml/min) with chloroform:acetone=8:2. After fractionating into 20 ml per tube, the product was confirmed using a phosphomolybdic acid color reaction using TLC (development solution chloroform:acetone=8:2). After concentrating a fraction which is No. 5-15 (100-300 ml) including the desired product, the product was freeze dried and 6-Trifluoroacetamidohexanoic acid was obtained (weight: 3.1 g yield: 89%).

Workup

  1. additionwas added
  2. customperformed at 30° C
  3. customAfter 72 hours had passed since the start of the reaction
  4. customthe reaction
  5. concentrationthe reaction solution was concentrated
  6. customAfter fractionating into 20 ml per tube
  7. customa phosphomolybdic acid color reaction
  8. concentrationAfter concentrating a fraction which
  9. customdried

Sources & evidence

ORD record
ord-37a01a5081354fd58e8035afae9a353a
Source dataset
uspto-grants-2013_05
Patent number
US08450441B2

Reaction notes

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