4-Methoxybenzenesulfonyl chloride → HCID 53813733, compound

HRID 1635064Notes

Reaction equation

HRID 1635064 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 hexaneyl 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 hexaneyl acetate)

Sources & evidence

ORD record
ord-d5766bc0d8384b43a58ec08b3ebca643
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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