Trifluoroacetic acid → 4-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamine

HRID 990079Notes

Reaction equation

HRID 990079 reaction equation
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:31]=[CH:30][C:19]([CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl.CO>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH2:22])=[CH:30][CH:31]=2)=[O:15])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12044207Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylcarbamate

Product 1

HCID 120442084-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamineYield 101.9%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the sulfoxide of Example 21 (0.92 g, 2.04 mmol) in dichloromethane (14 mL) and methanol (2 drops) was added trifluoroacetic acid (3.5 mL). This mixture was stirred for 4 h, and TLC indicated the absence of starting material. The volatile components were removed in vacuo and the residue was taken up into dichloromethane (50 mL) and washed with dilute aqueous sodium bicarbonate (2×). The organic phase was dried (Na2SO4), filtered and completely evaporated to leave 0.71 g of pure title compound.

Workup

  1. customThe volatile components were removed in vacuo
  2. washwashed with dilute aqueous sodium bicarbonate (2×)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customcompletely evaporated

Sources & evidence

ORD record
ord-db7b0ffd82cd4fa8a0ed920586864ef9
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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