Thioglycolic Acid → HCID 69666934, compound

HRID 860040Notes

Reaction equation

HRID 860040 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@@H:5](C1C=NC(OC)=CC=1)[CH2:6][N:7]([CH3:20])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH3:2].C([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])C.SC[C:39](O)=[O:40].[CH2:42](Cl)Cl>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@@H:6]([C:36]1[CH:35]=[N:32][C:33]([O:40][CH3:39])=[CH:34][CH:42]=1)[NH:7][CH3:20])[CH3:2]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 69666499HCID 69666499, compound

Product 1

HCID 69666934HCID 69666934, compound

Reagents, catalysts & solvents 1

HCID 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-468b960864e84f9e8227e8892d152b4b
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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