Trifluoroacetic acid water → (S)-1-(3-(3-chloro-4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)ethanamine

HRID 57397Notes

Reaction equation

HRID 57397 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([Cl:26])[CH:16]=2)[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.O>>[Cl:26][C:17]1[CH:16]=[C:15]([C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[O:14][N:13]=2)[CH:20]=[CH:19][C:18]=1[O:21][C:22]([F:23])([F:24])[F:25]

Participants

3

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 90454285HCID 90454285, compound

Product 1

HCID 90416650(S)-1-(3-(3-chloro-4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)ethanamine

Procedure

(S)-tert-butyl(1-(3-(3-chloro-4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)carbamate (2.0 g, 4.90 mmol) was treated with 90% TFA/water for 2 hours. Concentrate in vacuo and neutralized by passing through a column of MP-carbonate resin (6.0 g, 0.55 mmol/g eluting with MeOH/DCM/MeOH afforded 1.4 g waxy off-white solid. HRMS m/z 307.0335

Workup

  1. concentrationConcentrate in vacuo
  2. washeluting with MeOH/DCM/MeOH
  3. customafforded 1.4 g

Sources & evidence

ORD record
ord-fe85702cf98a40b499b5f8ca254add7e
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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