Trifluoroacetic acid → HCID 22482066, compound

HRID 2182149Notes

Reaction equation

HRID 2182149 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][C:17]([NH:20]C(OC(C)(C)C)=O)=[C:16]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][O:28][C:16]1[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[N:18][C:17]=1[NH2:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69732686HCID 69732686, compound

Product 1

HCID 22482066HCID 22482066, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5′-tert-Butoxycarbonylamino-6′-(3-chloro-benzyloxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-3q (50 mg, 96 μmol) was dissolved in CH2Cl2 (1 mL) and trifluoroacetic acid (1 mL) was added with stirring at room temperature. The solution was stirred at room temperature for 3 h then diluted with CH2Cl2 (20 mL). The CH2Cl2 solution was washed with saturated aqueous NaHCO3 (3×50 mL) and brine (25 mL), dried over Na2SO4 (anhydrous), filtered, and concentrated in vacuo to give the title compound 3-O as a reddish-brown solid (29 mg, 95% yield).

Workup

  1. stirringThe solution was stirred at room temperature for 3 h
  2. washThe CH2Cl2 solution was washed with saturated aqueous NaHCO3 (3×50 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4 (anhydrous)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48461de1a66b4668ab3e47f74dce2e5b
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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