Trifluoroacetic acid → HCID 11509792, compound

HRID 2403079Notes

Reaction equation

HRID 2403079 reaction equation
Cl.[SH:2][CH2:3][CH2:4]N.Cl[C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:27](F)(F)[C:28]([OH:30])=[O:29]>ClCCl>[C:8]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:2][C:3]2[CH:4]=[CH:9][C:8]([CH2:27][C:28]([OH:30])=[O:29])=[CH:7][CH:14]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6456Trityl chlorideHCID 9082Cysteamine Hydrochloride

Product 1

HCID 11509792HCID 11509792, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Mercaptoethylamine hydrochloride (261.4 mg, 2.3 mmol) was added to the solution of chloro triphenylmethane (557.6 mg, 2 mmol) in 1.0 mL of anhydrous dichloromethane. Then trifluoroacetic acid (TFA, 0.4 mL) was added to afford dark brown solution. The solution was stirred for 2 hrs under nitrogen. The reaction was quenched by 1N NaOH (3 mL). The suspension was extracted with 10 mL of ethyl acetate, and the organic phase was washed with brine (5 mL×3) and dried over anhydrous magnesium sulfate. The solvent was removed and residue was purified by flash chromatography on silica gel (eluent: ethyl acetate/hexane=⅓) to afford 543 mg of the desired product (85%). 1H NMR (400 MHz, CDCl3) δ 7.50-7.48 (m, 6H), 7.34-7.26 (m, 6H), 7.25-7.23 (m, 3H), 2.63 (t, J=6.5 Hz, 2H), 2.36 (t, J=6.5 Hz, 2H), ESI-MS: observed [M+Na]+: 342.5, calculated: 319.3.

Workup

  1. customto afford dark brown solution
  2. customThe reaction was quenched by 1N NaOH (3 mL)
  3. extractionThe suspension was extracted with 10 mL of ethyl acetate
  4. washthe organic phase was washed with brine (5 mL×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customresidue was purified by flash chromatography on silica gel (eluent: ethyl acetate/hexane=⅓)

Sources & evidence

ORD record
ord-d965138b0aad4cabbbb235cb02629dbf
Source dataset
uspto-grants-2014_08
Patent number
US08802387B2

Reaction notes

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