Trifluoroacetic acid → HCID 57554907, compound

HRID 1941774Notes

Reaction equation

HRID 1941774 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([N:22]1[CH2:28][CH2:27][CH2:26][C@@H:23]1[CH:24]=O)=O)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCCl.ClCCl.O>[O:1]([C:8]1[CH:9]=[C:10]([NH:11][CH2:24][C@H:23]2[CH2:26][CH2:27][CH2:28][NH:22]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinal

Product 1

HCID 57554907HCID 57554907, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-phenoxyaniline (0.3 g, 1.62 mmol) in 1,2-dichloroethane (4 ml) were added N-(tert-butoxycarbonyl)-D-prolinal (0.322 g, 1.62 mmol) and sodium triacetoxyborohydride (0.480 g, 2.26 mmol). The resulting suspension was stirred overnight at 50° C. The mixture was then cooled to room temperature, water (8 ml) was added and extracted with ethyl acetate (3×20 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30) to yield a light yellow oil that was dissolved in dichloromethane (4 ml). Trifluoroacetic acid (1 ml) was added and the mixture was stirred for 3 h at room temperature. Aqueous sodium hydroxide solution (4N) was added until basic pH and the mixture was extracted with ethyl acetate (2 times 30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate) to yield a colourless oil, (0.256 g, 59%); MS (ISP): 269.1 ((M+H)+.).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic layers were dried with magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30)
  7. customto yield a light yellow oil that
  8. stirringthe mixture was stirred for 3 h at room temperature
  9. extractionthe mixture was extracted with ethyl acetate (2 times 30 ml)
  10. dry with materialThe combined organic layers were dried with magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate)
  14. customto yield a colourless oil, (0.256 g, 59%)

Sources & evidence

ORD record
ord-89f9d6d5dc824ebf93f79dbed6927579
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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