Hydrochloric Acid → HCID 69591885, compound

HRID 1827591Notes

Reaction equation

HRID 1827591 reaction equation
C[O:2][C:3](=[O:33])[CH:4]=[CH: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:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24])(=[O:15])=[O:14])[C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:33])=[O:2])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69591931HCID 69591931, compound

Product 1

HCID 69591885HCID 69591885, compound

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}-acrylic acid methyl ester (0.040 g, 0.08 mmol) in 0.5 mL tetrahydrofuran was added sodium hydroxide (0.010 g, 0.25 mmol) in 0.5 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 dried (magnesium sulfate) and concentrated. Preparative TLC afforded 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid. 1H NMR (CDCl3) δ 7.58 (d, 1H, J=16 Hz), 7.29 (d, 2H, J=8.4 Hz), 7.04 (d, 2H, J=8.4 Hz), 7.05–7.00 (m, 1H), 6.86 (s, 2H), 6.70–6.60 (m, 3H), 6.28 (d, 1H, J=16 Hz), 4.77 (s, 2H), 2.45 (s, 6H), 2.25 (s, 3H).

Workup

  1. additionwas added
  2. washThe aqueous solution was washed with methylene chloride
  3. dry with materialthe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbef8af85dba40869303ea5838c3be40
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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