Lithium hydroxide, monohydrate → [Methyl-(toluene-4-sulfonyl)-amino]-acetic acid

HRID 81862Notes

Reaction equation

HRID 81862 reaction equation
[CH3:1][N:2]([CH2:13][C:14]([O:16]C)=[O:15])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].O[Li].O>CO.C1COCC1.O>[CH3:1][N:2]([CH2:13][C:14]([OH:16])=[O:15])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 3277444Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetate

Product 1

HCID 802555[Methyl-(toluene-4-sulfonyl)-amino]-acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl ester 6 (2.60 g, 10.1 mmol) was dissolved in a 3:1:1 mixture of MeOH-THF—H2O. LiOH.H2O (0.53 g, 12.6 mmol) was added at room temperature and the reaction allowed to stir for 3 h. All solvents were evaporated, apart from water. The remaining aqueous solvent was diluted further and thoroughly washed with ethyl acetate. The aqueous basic aqueous layer was then acidified to pH 2 with 1 M HCl and the product extracted with ethyl acetate. The organic layers were then combined and dried over Na2SO4, filtered and concentrated to afford the title compound. (2.33 g, 95%): δH (400 MHz, CDCl3) 2.43 (s, 3H, CH3), 2.87 (s, 3H, CH3), 3.99 (s, 2H, CH2), 7.32 (d, J=8.0 Hz, 2H, CH), 7.69 (d, J=8.0 Hz, 2H, CH); δC (100 MHz, CDCl3) 21.4, 35.7, 50.6, 127.3, 129.6, 134.8, 143.7, 173.5; LRMS (ES+) calcd for [C10H13NO4S+H] 244.06. found 244.07 [M+H].

Workup

  1. customAll solvents were evaporated, apart from water
  2. additionThe remaining aqueous solvent was diluted further
  3. washthoroughly washed with ethyl acetate
  4. extractionthe product extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3bdff2d074c44c9987c94d2ad11978b5
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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