Hydrochloric Acid → HCID 22137298, compound

HRID 1827594Notes

Reaction equation

HRID 1827594 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[S:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[OH-].[Na+].Cl>O1CCCC1.O>[OH:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][N:12]([S:13]([C:16]1[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=1[CH3:22])(=[O:15])=[O:14])[C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23579139HCID 23579139, compound

Product 1

HCID 22137298HCID 22137298, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid methyl ester (0.017 g, 0.04 mmol) in 0.5 mL tetrahydrofuran was added sodium hydroxide (0.004 g, 0.11 mmol) in 0.1 mL water. The reaction was stirred at room temperature for 24 hr. The reaction mixture was adjusted to a pH of 4 with 1N HCl and water was added. The aqueous solution was washed with methylene chloride and the organic layer was concentrated to afford 0.015 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid. 1H NMR (CDCl3) δ 7.05 (t, 1H, J=7.6 Hz), 7.00–6.93 (m, 2H), 6.90–6.80 (m, 4H), 6.70–6.62 (m, 2H), 6.43 (bs, 1H), 4.69 (s, 2H), 2.83 (t, 2H, J=7.2 Hz), 2.56 (t, 2H, J=7.2 Hz), 2.42 (s, 6H), 2.24 (s, 3H).

Workup

  1. additionwas added
  2. washThe aqueous solution was washed with methylene chloride
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-cfbc8ed4d2914ea4b33ae27b58500296
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

Loading…