4-Methoxybenzenesulfonyl chloride → HCID 53813733, compound

HRID 343622Notes

Reaction equation

HRID 343622 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:9])[CH2:7][NH:8][S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 151417Glycine tert-butyl ester

Product 1

HCID 53813733HCID 53813733, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of glycine t-butyl ester (5.0 grams, 29.82 mmol) in methylene chloride (50 ml) is added triethylamine (6.65 ml, 62.63 mmol) followed by 4-methoxybenzenesulfonyl chloride (29.82 mmol, 6.2 grams). The solution is stirred for 24 hours, diluted with water and extracted with ethyl acetate. The combined extracts are dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with 6:1 hexane-ethyl acetate) to provide (4-methoxybenzenesulfonylamino) acetic acid t-butyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel chromatography (elution with 6:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bfa589a1bf5647729c4742865e204047
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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