Tert-butyl 2-(pyridin-3-yl)acetate → (R)-2-((R)-2-tert-Butoxy-2-oxo-1-(pyridin-3-yl)ethyl)-5,5,5-trifluoropentanoic acid

HRID 2276878Notes

Reaction equation

HRID 2276878 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:2]=1.[F:15][C:16]([F:39])([F:38])[CH2:17][CH2:18][C@@H:19](OS(C(F)(F)F)(=O)=O)[C:20]([O:22]CC1C=CC=CC=1)=[O:21]>>[C:11]([O:10][C:8](=[O:9])[C@H:7]([C@@H:19]([CH2:18][CH2:17][C:16]([F:39])([F:38])[F:15])[C:20]([OH:22])=[O:21])[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 11542918Tert-butyl 2-(pyridin-3-yl)acetateHCID 90086998(R)-benzyl 5,5,5-trifluoro-2-(trifluoromethylsulfonyloxy)pentanoate

Product 1

HCID 90079979(R)-2-((R)-2-tert-Butoxy-2-oxo-1-(pyridin-3-yl)ethyl)-5,5,5-trifluoropentanoic acid

Procedure

Intermediate S-3 was synthesized from tert-butyl 2-(pyridin-3-yl)acetate (100 mg, 0.517 mmol) and (R)-benzyl 5,5,5-trifluoro-2-(trifluoromethylsulfonyloxy)pentanoate (245 mg, 0.621 mmol) using the procedure described for Intermediate S-2 to give Intermediate S-3 (60 mg, 0.173 mmol) as a white solid containing about 30% of the (R, S) isomer. MS(ES):m/z=483.3 [M+H+].

Workup

  1. customto give Intermediate S-3 (60 mg, 0.173 mmol) as a white solid
  2. additioncontaining about 30% of the (R, S) isomer

Sources & evidence

ORD record
ord-cebff4e5742c46f2b87f9931987b4b9f
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

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