Glyoxylic Acid → HCID 66878721, compound

HRID 2265890Notes

Reaction equation

HRID 2265890 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:36]([OH:40])(=[O:39])[CH:37]=O>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([S:13]([N:16]3[CH2:17][CH2:18][C:19]4[C:24](=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]4)[CH:37]3[C:36]([OH:40])=[O:39])(=[O:15])=[O:14])=[CH:11][CH:12]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 66879410HCID 66879410, compound

Product 1

HCID 66878721HCID 66878721, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

110 mg (0.221 mmol) of 4-(4-fluorophenoxy)-N-{2-[2-(2-piperidin-1-ylethoxy)phenyl]-ethyl}benzenesulfonamide are stirred together with 49.1 μl (0.441 mmol) of glyoxylic acid (50% strength in H2O) in 5 ml of trifluoroacetic acid at room temperature. After standing overnight, the mixture is concentrated in vacuo and the residue is chromatographed on silica gel, resulting in the desired carboxylic acid in a yield of 52%.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-8b2f1480f5be43beb079070bbc1e8561
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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