Hydrochloric Acid → HCID 66610326, compound

HRID 76171Notes

Reaction equation

HRID 76171 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].Cl>CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([NH2:20])[CH3:19])=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66610473Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate

Product 1

HCID 66610326HCID 66610326, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 25.0 g (62.90 mmol) tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate (I62) in 375 mL EtOAc are added 79 mL (315 mmol) HCl (4M in dioxane). The mixture is stirred at r.t. over night, filtered and the obtained precipitate is dried. The crude product is suspended in DCM and sat. NaHCO3 is added until a clear solution is obtained. The layers are separated and the aqueous layer is extracted two more times with DCM. The organic layers are combined, washed with brine (1×), dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, heptane/EtOAc/TEA 75/25/1→0/100/1).

Workup

  1. filtrationfiltered
  2. customthe obtained precipitate is dried
  3. additionsat. NaHCO3 is added until a clear solution
  4. customis obtained
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted two more times with DCM
  7. washwashed with brine (1×)
  8. dry with materialdried with Na2SO4
  9. customthe solvent is removed in vacuo
  10. customThe residue is purified by column chromatography (silica gel, heptane/EtOAc/TEA 75/25/1→0/100/1)

Sources & evidence

ORD record
ord-7308b56f792148c8b8fc51747b10a44c
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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