Trifluoroacetic acid → HCID 66969863, compound

HRID 402217Notes

Reaction equation

HRID 402217 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:6][CH:5]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl-:1].[Cl:1][CH2:2][CH2:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH3+:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59791338HCID 59791338, compound

Product 1

HCID 66969863HCID 66969863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 2-{2-[4-(2-chloroethyl)phenoxy]-ethoxy}ethylcarbamate (1.7 mmol) was dissolved in 5 ml dichloromethane and triethylsilane (0.5 ml, 5% v/v) was added. At this point trifluoroacetic acid (5 ml) was added dropwise to the solution at room temperature. The reaction mixture turned golden brown upon addition and was allowed to stir for one hour. All volatiles were removed under reduced atmosphere, the residue was re-dissolved in CH2Cl2, and washed twice with dilute HCl. The aqueous fractions were lyophilized overnight. The remaining oily residue was dissolved in anhydrous DMF to be used as a stock solution in further reactions.

Workup

  1. additionThe reaction mixture turned golden brown upon addition
  2. customAll volatiles were removed under reduced atmosphere
  3. dissolutionthe residue was re-dissolved in CH2Cl2
  4. washwashed twice with dilute HCl
  5. waitThe aqueous fractions were lyophilized overnight
  6. dissolutionThe remaining oily residue was dissolved in anhydrous DMF

Sources & evidence

ORD record
ord-79d40019d5324a6a85cd96bc68fdc0b4
Source dataset
uspto-grants-2014_06
Patent number
US08742086B2

Reaction notes

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