Water → HCID 86627345, compound

HRID 1896007Notes

Reaction equation

HRID 1896007 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH:9]=[C:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[C:1]1(/[CH:7]=[CH:8]/[CH:9]=[C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86627344HCID 86627344, compound

Product 1

HCID 86627345HCID 86627345, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Compound 255a (752 mg, 2.51 mmol) in CHCl3 (15 mL) was added trifluoroacetic acid (0.967 mL, 12.6 mmol) and the reaction mixture was stirred at 25° C. for 24 h, until the complete conversion of the reagent was observed by LC-MS. Water was added followed by aq. NaOH (2 N) to give alkaline pH. Separation of the organic layer and extraction of the aqueous layer with CH2Cl2, washing with brine and drying over Na2SO4 the combined organic layers, afforded the title compound. The crude was purified by flash chromatography (CHCl3-1.6 M methanolic ammonia 100:5) affording the title product (359 mg).

Workup

  1. customto give alkaline pH
  2. customSeparation of the organic layer and extraction of the aqueous layer with CH2Cl2
  3. washwashing with brine
  4. dry with materialdrying over Na2SO4 the combined organic layers

Sources & evidence

ORD record
ord-d1b46ee2f4b6477ea8c8e34d7716cfe3
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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