Trifluoroacetic acid → 1-(3-Phenyl-1,2-oxazol-5-yl)methanamine

HRID 2111672Notes

Reaction equation

HRID 2111672 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][CH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672837925-(tert-Butoxycarbonylaminomethyl)-3-phenylisoxazole

Product 1

HCID 27641651-(3-Phenyl-1,2-oxazol-5-yl)methanamineYield 141.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.7 ml, 2.6 mmol) was added dropwise to a solution of 5-(tert-butoxycarbonylaminomethyl)-3-phenylisoxazole (Method 43; 473 mg, 1.73 mmol) in DCM (8 ml) cooled in an ice bath. The mixture was warmed to ambient temperature and stirred for 18 hours and the volatiles removed by evaporation. The residue was triturated with ether to give the title compound (427 mg, 86%). NMR (DMSO) 4.33 (s, 2H), 7.1 (s, 1H), 7.5 (m, 3H), 7.8 (m, 2H), 8.6 (br s, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. customthe volatiles removed by evaporation
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-ca4fd63d70514e33a8f4947a3b8d19a2
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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