Cornforth reagent → HCID 86695179, compound

HRID 1504023Notes

Reaction equation

HRID 1504023 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:16][C:15]2[C:14]3[C:13]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]4)=[N:12][CH:11]=[N:10][C:9]=3[S:8][C:7]=2[CH2:6][CH2:5]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:44][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CN(C=O)C>[C:27]([O:26][C:25]([NH:24][CH:21]1[CH2:20][CH2:19][CH:18]([O:17][C:13]2[C:14]3[C:15]4[CH2:16][C@H:4]([CH2:3][C:2]([OH:44])=[O:1])[CH2:5][CH2:6][C:7]=4[S:8][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:23][CH2:22]1)=[O:31])([CH3:28])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86695177tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate

Product 1

HCID 86695179HCID 86695179, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added tert-butyl N-(4-[[(12R)-12-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (129 mg, 0.29 mmol, 1.00 equiv) in 4 mL of DMF. Then PDC (639 mg, 1.70 mmol, 6.00 equiv) was added and the resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and extracted with 4×40 mL of CHCl3/isopropanol (3:1). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to provide 2-[(12R)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetic acid (98 mg, 74%) as an off-white solid.

Workup

  1. customTo a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched with water
  4. extractionextracted with 4×40 mL of CHCl3/isopropanol (3:1)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-faf90f9e1a8d4aed8c89972fc016264a
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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