Thioglycolic Acid → HCID 66616094, compound

HRID 2367068Notes

Reaction equation

HRID 2367068 reaction equation
[CH3:1][C:2]1([CH3:43])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:41])[C@@H:18]([N:27]([CH3:40])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)[C:3]1=[O:42].SCC(O)=O.O.[OH-].[Li+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1([CH3:43])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:41])[C@@H:18]([NH:27][CH3:40])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:16]2)[C:3]1=[O:42]

Participants

7

Reactant 3

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 66616133HCID 66616133, compound

Product 1

HCID 66616094HCID 66616094, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (S)—N-(1-(4-(3,3-dimethyl-2-oxoindolin-1-yl)piperidin-1-yl)-1-oxo-4-phenylbutan-2-yl)-N-methyl-2-nitrobenzenesulfonamide (3.30 g, with triphenylphosphineoxide as impurity, EXAMPLE 73, Step 2) in dimethyl formamide (10 mL) were added mercaptoacetic acid (491 mg, 5.33 mmol) and lithium hydroxide monohydrate (447 mg, 10.7 mmol) at room temperature. After stirring for 16 h, the mixture was diluted with ethyl acetate and saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and brine, dried over sodium sulfate and concentrated in vacuo. The residue was diluted with dichloromethane (10 mL) and to the solution was added hydrogen chloride in methanol. Then the mixture was concentrated. The residue was diluted with methanol, and mixed with strong cation exchange gel (BondeSil(registered trademark) SCX, 40 g, Varian Inc.). The gel was filtered and washed with 1 mol/L ammonia in methanol, and the solution was concentrated to give the title compound (636 mg, 71%).

Workup

  1. washThe organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with dichloromethane (10 mL) and to the solution
  5. additionwas added hydrogen chloride in methanol
  6. concentrationThen the mixture was concentrated
  7. additionThe residue was diluted with methanol
  8. additionmixed with strong cation exchange gel (BondeSil(registered trademark) SCX, 40 g, Varian Inc
  9. filtrationThe gel was filtered
  10. washwashed with 1 mol/L ammonia in methanol
  11. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-442c6997ebfe4e62ad9366f59e7643de
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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