Hydrochloric Acid → HCID 10228125, compound

HRID 2215107Notes

Reaction equation

HRID 2215107 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][N:5]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[Cl:28])(=[O:20])=[O:19])[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12]2.O.[OH-].[Na+].Cl>C1COCC1>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([S:18]([N:5]([CH2:4][C:3]([OH:29])=[O:2])[CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH2:13][CH2:12]3)(=[O:19])=[O:20])=[C:22]([Cl:28])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68533036HCID 68533036, compound

Product 1

HCID 10228125HCID 10228125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of {(4-bromo-2-chloro-benzenesulfonyl)-[2-(indan-5-yloxy)-ethyl]-amino}-acetic acid methyl ester (2.8 g) in THF (22 ml)-water (22 ml) at 15° C. is treated dropwise with 1 M aqueous sodium hydroxide solution (28 ml), and the resulting mixture stirred for 3 hours. The mixture is then diluted with ice-cold water (200 ml), acidified to pH 1 with 1 M hydrochloric acid, and extracted with ethyl acetate (2×100 ml). The combined extracts are washed successively with water (100 ml) and then brine, dried over magnesium sulfate, filtered and evaporated. The resulting solid is triturated with hexane, collected by filtration and dried, to afford {(4-bromo-2-chloro-benzenesulfonyl)-[2-(indan-5-yloxy)-ethyl]-amino}-acetic acid [retention time 7.6 min/HPLC conditions: Kingsorb 3 micron, 30×4.6 mm C 18 column, Gradient elution 10 to 100% acetonitrile in water (+0.1% trifluoroacetic acid) over 10 min]. 1H NMR (DMSO-d6) δ=12.88 (broad s, 1H), 7.94 (d, 1H), 7.90 (d, 1H), 7.71 (dxd, 1H), 7.03 (d, 1H), 6.50 (s, 1H), 6.43 (dxd, 1H), 4.26 (s, 2H), 3.97 (t, 2H), 3.65 (t, 2H), 2.79 (t, 2H), 2.75 (t, 2H), 1.98 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined extracts are washed successively with water (100 ml)
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting solid is triturated with hexane
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-94fba13d80b54e2bbbee433af941887e
Source dataset
uspto-grants-2006_09
Patent number
US07109203B2

Reaction notes

Loading…