Dimethylformamide → [4-(4-Fluoro-benzyloxy)-benzenesulfonylamino]-acetic acid tert-butyl ester

HRID 2269320Notes

Reaction equation

HRID 2269320 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].CN(C=O)C.C(N(CC)CC)C.[F:23][C:24]1[CH:41]=[CH:40][C:27]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1>C(OCC)(=O)C>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][S:36]([C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:28][C:27]2[CH:40]=[CH:41][C:24]([F:23])=[CH:25][CH:26]=2)=[CH:31][CH:32]=1)(=[O:37])=[O:38])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 181794244-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

Product 1

HCID 54478351[4-(4-Fluoro-benzyloxy)-benzenesulfonylamino]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of glycine tert butyl ester hydrochloride salt (5.9 g, 18 mmol) and DMF (20 mL) at 0° C. was added triethylamine (6.5 mL, 45 mmol) and 4-(4-fluoro-benzyloxy)-benzenesulfonyl chloride. After stirring for 1 h, the mixture was warmed to room temperature and stirred for an additional hour. The mixture was diluted with ethyl acetate, washed with 1M HCl, saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Trituration of the residue with ether-hexane afforded 10.8 g of [4-(4-fluoro-benzyloxy)-benzenesulfonylamino]-acetic acid tert-butyl ester as colorless crystals.

Workup

  1. stirringstirred for an additional hour
  2. washwashed with 1M HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20a77ce96df14d72b383ffd02d16dfb1
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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