Potassium tert-butoxide → HCID 59263266, compound

HRID 643891Notes

Reaction equation

HRID 643891 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([N:20]3[CH2:24][C:23](=[O:25])[NH:22][S:21]3(=[O:27])=[O:26])=[C:14]([OH:19])[CH:15]=2)[CH:10]=1)[CH3:2].[CH3:29]C([O-])(C)C.[K+]>CC(O)C>[CH:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([N:20]3[CH2:24][C:23](=[O:25])[NH:22][S:21]3(=[O:26])=[O:27])=[C:14]([OH:19])[CH:15]=2)[CH:10]=1)([CH3:29])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59263265HCID 59263265, compound

Product 1

HCID 59263266HCID 59263266, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirring solution of 5-[6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-pentanoic acid ethyl ester (0.003 g, 0.007 mmol) in iPrOH (1 mL) is added t-BuOK (1M in THF, 0.044 mL). The mixture is stirred for 18 h at room temperature. The reaction is quenched with 1 N HCl (1.5 mL) and extracted with EtOAc (3×10 mL). The organic layers are dried and concentrated. The residue is passed through a short column of reverse phase silica gel eluting with 40% MeOH/H2O to afford 5-[6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-pentanoic acid isopropyl ester: Retention time=1.17 min (Method A); (M−H)−=419.

Workup

  1. customThe reaction is quenched with 1 N HCl (1.5 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. customThe organic layers are dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5169a026194c46e0bd099f71e89b2d2b
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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