Thioglycolic Acid → HCID 69666934, compound

HRID 2120650Notes

Reaction equation

HRID 2120650 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[N:7]([CH3:20])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH3:2].C(N(CC)CC)C.SCC(O)=O>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[NH:7][CH3:20])[CH3:2]

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 69774812HCID 69774812, compound

Product 1

HCID 69666934HCID 69666934, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sulfonamide 1-7 (4.7 gm, 10 mmol) in CH2Cl2 (50 mL) was treated with triethylamine (2.8 mL, 20 mmol) and mercaptoacetic acid (1.04 mL, 15 mmol). The reaction was stirred for 90 min at room temperature. The green solution was diluted with EtOAc (500 mL) and washed with satd aqueous NaHCO3 (150 mL), water (3×100 mL), and brine (3×100 mL). The solution was dried over Na2SO4, filtered and concentrated to a black oil. The residue was purified by flash chromatography (5% MeOH/CH2Cl2) to give the desired product 1-8.

Workup

  1. washwashed with satd aqueous NaHCO3 (150 mL), water (3×100 mL), and brine (3×100 mL)
  2. dry with materialThe solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a black oil
  5. customThe residue was purified by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d53e0e984777432fa1f34f9785c08223
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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