Trifluoroacetic acid → HCID 86747172, compound

HRID 2255727Notes

Reaction equation

HRID 2255727 reaction equation
CC(C)=CC(N[CH:7]([NH2:26])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15]CCCC(OC(C)(C)C)=O)=O.[S:28]1[CH:32]=[CH:31]C=[C:29]1[CH2:33][C:34](O)=O.C(S[C:41]([CH3:67])([CH3:66])[CH2:42][C:43]([NH:45]C(N)CCOCCCCOCCCC(OC(C)(C)C)=O)=[O:44])(=O)C.FC(F)(F)C(O)=[O:71]>C(OCC)C>[C:32]([S:28][CH:29]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][CH2:7][NH2:26])[CH2:33][CH2:34][NH:45][C:43](=[O:44])[CH2:42][CH:41]([CH3:67])[CH3:66])(=[O:71])[CH3:31]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159702-Thiopheneacetic acidHCID 86747173HCID 86747173, compoundHCID 86747174HCID 86747174, compound

Product 1

HCID 86747172HCID 86747172, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1-dimethylacrylamido-12-BOC-amino-4,9-dioxadodecane (0.6 g, 1.6 mmole) in a 25 ml round bottom flask was added 10 ml of freshly distilled thiolacetic acid. The solution was stirred and refluxed under nitrogen for four hours. The solution was cooled and diluted to 70 ml with diethyl ether. The ether solution was washed with water, 5% acetic acid, water, and saturated sodium chloride solution, and dried over magnesium sulfate. Concentration gave a pale brown oil: 1-(3-acetylthio-3-methylbutyramido)-12-BOC-amino-4,9-dioxadodecane (4). This crude product was stirred with 5 ml trifluoroacetic acid for 1/2 hour at room temperature. The TFA was removed by evaporation with a stream of nitrogen. Yield (crude product)=0.59 g (1.6 mmole, ~100%) of 1-(3-acetylthio-3-methylbutyramido-12-amino-4,9-dioxadodecane (5).

Workup

  1. temperaturerefluxed under nitrogen for four hours
  2. temperatureThe solution was cooled
  3. washThe ether solution was washed with water, 5% acetic acid, water, and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration
  6. customgave a pale brown oil
  7. customThe TFA was removed by evaporation with a stream of nitrogen

Sources & evidence

ORD record
ord-0cd0c2b0cfaf44e9937ee7ebc9909ce7
Source dataset
uspto-grants-1993_08
Patent number
US05241078

Reaction notes

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