Trifluoroacetic acid → HCID 69423910, compound

HRID 1765684Notes

Reaction equation

HRID 1765684 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH:11]([C:13]1[O:17][N:16]=[C:15]([CH2:18][CH3:19])[N:14]=1)[OH:12])[CH2:9][CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C1(C)C=CC=CC=1>[NH2:7][CH:8]([CH2:9][CH3:10])[C@@H:11]([C:13]1[O:17][N:16]=[C:15]([CH2:18][CH3:19])[N:14]=1)[OH:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60054545HCID 60054545, compound

Product 1

HCID 69423910HCID 69423910, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)-hydroxy-methyl]-propyl}-carbamic acid tert-butyl ester (3.67 g, 12.87 mmol) in dichloromethane (50 mL) was treated with trifluoroacetic acid (10 mL) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with toluene then evaporated under vacuum to dryness. The residue was dissolved in dichloromethane (75 mL) and the solution was treated with MP-Carbonate (3.3 mmol/g, 6.0 g). This mixture was stirred at room temperature overnight, then filtered, then washed with 10% dichloromethane methanol and evaporated under vacuum to give (S)-2-amino-1-(3-ethyl-1,2,4-oxadiazol-5-yl)-butan-1-ol, a mixture of diastereomers, (2.26 g). 1H NMR [(CD3)2SO]: δ 4.61 and 4.54 (d, J=5 Hz, 1H), 2.86 (m, 1H), 2.71 (q, J=8 Hz, 2H), 1.6–1.0 (2×m, 2H), 1.22 (t, J=8 Hz, 3H), 0.88 (m, 3H). MS m/z 186 (M+H).

Workup

  1. customthen evaporated under vacuum to dryness
  2. dissolutionThe residue was dissolved in dichloromethane (75 mL)
  3. additionthe solution was treated with MP-Carbonate (3.3 mmol/g, 6.0 g)
  4. stirringThis mixture was stirred at room temperature overnight
  5. filtrationfiltered
  6. washwashed with 10% dichloromethane methanol
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-5f071355dbc649dc8e76059b29d79739
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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