Trifluoroacetic acid → HCID 69717599, compound

HRID 2085991Notes

Reaction equation

HRID 2085991 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:8][C:9]2[C:10]([CH2:15][S:16][CH2:17][CH2:18][NH:19]C(OC(C)(C)C)=O)=[N:11][CH:12]=[CH:13][CH:14]=2)C=CC=CC=1.C([SiH](CC)CC)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>ClCCl>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[SH:8][C:9]1[C:10]([CH2:15][S:16][CH2:17][CH2:18][NH2:19])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 99372073-Triphenylmethylthio-2-(t-butoxycarbonylaminoethylthiomethyl)pyridine

Product 1

HCID 69717599HCID 69717599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 1 L round bottom flask equipped with a mechanical stirrer, thermometer and nitrogen purge was charged 3-triphenylmethylthio-2-(t-butoxycarbonylaminoethylthiomethyl)pyridine (40.0 g, 0.074 mol, 1 eq) followed by dichloromethane (200 mL). The light yellow solution was cooled to 0° C. and triethylsilane (60 mL) was added followed by dropwise addition of trifluoroacetic acid (200 mL) over approximately five minutes. The cold bath was removed and the solution was allowed to warm to room temperature (over 30 minutes) and was then allowed to stir at 20° C. for 30 minutes. The solvent was removed by rotary evaporation to give 27.75 g of the title compound as an orange waxy solid. 1H NMR (D2O) δ 2.88 (t, 2H); 3.28 (t, 3H); 4.18 (s, 2H); 7.45 (dd, 1H); 8.22 (d, 1H); 8.55 (d, 1H).

Workup

  1. customInto a 1 L round bottom flask equipped with a mechanical stirrer
  2. customthermometer and nitrogen purge
  3. customThe cold bath was removed
  4. temperatureto warm to room temperature (over 30 minutes)
  5. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-65d49389f23248e8b84cddd9899975a0
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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