Sodium Hydroxide → 2-(4-{[(3-Carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic Acid Ethyl Ester

HRID 23794Notes

Reaction equation

HRID 23794 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])[CH:27]=2)[S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2].[OH-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:41])[C:5]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][C:34]([OH:36])=[O:35])[CH:27]=2)[S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:18])=[CH:12][CH:13]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 697317692-(4-{[(3-Tert-butoxycarbonylmethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 697316782-(4-{[(3-Carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(4-{[(3-tert-butoxycarbonylmethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid ethyl ester (138 mg, 0.237 mmol) in MeOH (5 mL) was added aqueous NaOH (2N, 0.36 mL, 0.72 mmol). The reaction was heated at 100° C. for 1 h and was cooled to room temperature. The reaction was concentrated in vacuo and was diluted with water and EtOAc. The pH was adjusted to about 5 with 1N HCl. The aqueous solution was washed with EtOAc (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Sodium chloride was added to the aqueous solution and the solution was washed with EtOAc (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. The combined title compound (104 mg) was used in the next step without further purification. MS 527 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. additionwas diluted with water and EtOAc
  4. washThe aqueous solution was washed with EtOAc (3×)
  5. dry with materialThe combined organic solutions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionSodium chloride was added to the aqueous solution
  9. washthe solution was washed with EtOAc (3×)
  10. dry with materialThe combined organic solutions were dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-fa2a2fdca3814a6fa7faf9870daf0e1d
Source dataset
uspto-grants-2005_02
Patent number
US06852863B2

Reaction notes

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