Sodium Methoxide → HCID 131730318, compound

HRID 1948312Notes

Reaction equation

HRID 1948312 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C:17]2[NH:18][C:19]([CH3:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])=[O:16])[C@H:10]([CH2:25][O:26]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][O-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C:17]2[NH:18][C:19]([CH3:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])=[O:16])[C@H:10]([CH2:25][O:26][CH3:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131730316HCID 131730316, compound2×

Product 1

HCID 131730318HCID 131730318, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Cis-tert-butyl-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (Intermediate 72; 325 mg) was dissolved in 5 ml of a 30 wt % MeOH solution containing NaOMe and an additional 5 ml of dry MeOH. The homogeneous reaction was stirred at room temperature for 2 days. Upon reacting, solids began to precipitate from solution. The reaction was concentrated to a solid residue, re-dissolved in EtOAc and washed with saturated NH4Cl (2×10 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The residual material was purified by flash column chromatography eluting with (1:1 EtOAc/hexanes) to give the title compound (192 mg). MS (ES)(MH+): 420 for C19H27Cl2N3O4.

Workup

  1. customThe homogeneous reaction
  2. customto precipitate from solution
  3. concentrationThe reaction was concentrated to a solid residue
  4. dissolutionre-dissolved in EtOAc
  5. washwashed with saturated NH4Cl (2×10 ml)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residual material was purified by flash column chromatography
  10. washeluting with (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-f99858c9d20f4beeada59845b4b164c1
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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