Trifluoroacetic acid → HCID 59556658, compound

HRID 1172944Notes

Reaction equation

HRID 1172944 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH:26][CH2:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([S:23]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])(=[O:25])=[O:24])=[CH:21][CH:22]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53245844HCID 53245844, compound

Product 1

HCID 59556658HCID 59556658, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoate (0.28 g, 0.536 mmol) in dichloromethane (6.0 ml) was added TFA (2.0 ml, 26.0 mmol). After about 3 h the reaction mixture was concentrated in vacuo and the resulting solid was triturated with ether, filtered and dried to provide 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoic acid (0.176 g, 70%) as a colorless solid. LCMS (Table 1, Method c) Rt=2.54 min, m/z 466 (M+H)+.

Workup

  1. concentrationAfter about 3 h the reaction mixture was concentrated in vacuo
  2. customthe resulting solid was triturated with ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-21f889e78378477da2d49a97c1554b9e
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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