Trifluoroacetic acid → HCID 68543717, compound

HRID 2243499Notes

Reaction equation

HRID 2243499 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:24][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH:16]C(OC(C)(C)C)=O)[C:14]=3[S:15][C:7]=2[C:6]=1[O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:24][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH2:16])[C:14]=3[S:15][C:7]=2[C:6]=1[O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68544784HCID 68544784, compound

Product 1

HCID 68543717HCID 68543717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step H Deprotection: A solution of 7-tert-Butoxycarbonylamino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (170 mg, 0.37 mmol) in DCM (6 mL) was cooled to 0° C. Trifluoroacetic acid (1.2 mL) was then added, and the solution was allowed to warm to ambient temperature, stirring a total of four hours, after which the reaction was judged complete by TLC. The reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, and washed with sodium bicarbonate (3×10 mL). The organic layer was then concentrated in vacuo, affording 7-Amino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester in a quantitative yield.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with sodium bicarbonate (3×10 mL)
  4. concentrationThe organic layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-25775d23cdfc4069847bfd019f56f67d
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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