Trifluoroacetic acid → HCID 59556660, compound

HRID 1172945Notes

Reaction equation

HRID 1172945 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([NH:33][CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])(=[O:32])=[O:31])=[CH:26][CH:25]=3)[O:21][N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[N:23]=[C:22]([C:24]3[CH:25]=[CH:26][C:27]([S:30]([NH:33][CH2:34][C:35]([OH:37])=[O:36])(=[O:32])=[O:31])=[CH:28][CH:29]=3)[O:21][N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59556617HCID 59556617, compound

Product 1

HCID 59556660HCID 59556660, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.0 ml, 26.0 mmol) was added dropwise to a stirred mixture of tert-butyl 2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)acetate (0.121 g, 0.238 mmol), DCM (5.0 ml) under N2. The mixture was stirred at ambient temperature for 3 hrs then concentrated in vacuo. The resulting solid was triturated in ether, filtered and dried to yield 2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)acetic acid (46 mg, 0.102 mmol) as a white solid. LCMS (Table 1, Method c) Rt=2.14 min, m/z 450.34 (M−H)−

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting solid was triturated in ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-72554922380b4f5981c804043f3bb412
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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