Trifluoroacetic acid water → HCID 86269207, compound

HRID 57490Notes

Reaction equation

HRID 57490 reaction equation
C([O:5][C@@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[C:19]([F:20])=[CH:18][N:17]=[C:16]([NH:21][CH:22]([C:24]2[O:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[CH:27][N:28]=2)[CH3:23])[N:15]=1)[CH3:7])(C)(C)C.C(O)(C(F)(F)F)=O.O>>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[O:25][C:24]([C@H:22]([NH:21][C:16]3[N:15]=[C:14]([N:9]4[C@@H:8]([C@H:6]([OH:5])[CH3:7])[CH2:12][O:11][C:10]4=[O:13])[C:19]([F:20])=[CH:18][N:17]=3)[CH3:23])=[N:28][CH:27]=2)=[CH:30][CH:31]=1.[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[O:25][C:24]([C@@H:22]([NH:21][C:16]3[N:15]=[C:14]([N:9]4[C@@H:8]([C@H:6]([OH:5])[CH3:7])[CH2:12][O:11][C:10]4=[O:13])[C:19]([F:20])=[CH:18][N:17]=3)[CH3:23])=[N:28][CH:27]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 90416257(4R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-((1-(5-(4-chlorophenyl)oxazol-2-yl)ethyl)amino)-5-fluoropyrimidin-4-yl)oxazolidin-2-one

Product 2

HCID 86269207HCID 86269207, compoundHCID 90416338HCID 90416338, compound

Procedure

(4R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-((1-(5-(4-chlorophenyl)oxazol-2-yl)ethyl)amino)-5-fluoropyrimidin-4-yl)oxazolidin-2-one (124 mg, 0.246 mmol) was treated with 90% TFA/water for 2 hours. Concentrated in vacuo and neutralized by passing through a column of MP-carbonate resin (2.0 g, 0.55 mmol/g eluting with MeOH/DCM/MeOH afforded the diastereomeric mixture. Chiral SFC chromatography on an ID column (75 g/min, 120 bar, 21×250 mm) eluting 45% IPA/CO2 (v/v) to give (R)-3-(2-(((R)-1-(5-(4-chlorophenyl)oxazol-2-yl)ethyl)amino)-5-fluoropyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one and (R)-3-(2-(((S)-1-(5-(4-chlorophenyl)oxazol-2-yl)ethyl)amino)-5-fluoropyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one.

Workup

  1. concentrationConcentrated in vacuo
  2. washeluting with MeOH/DCM/MeOH
  3. customafforded the diastereomeric mixture
  4. washChiral SFC chromatography on an ID column (75 g/min, 120 bar, 21×250 mm) eluting 45% IPA/CO2 (v/v)

Sources & evidence

ORD record
ord-3ca7f4dda9554126b771d0f87e819b21
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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