HCID 53697450, compound → HCID 22246720, compound

HRID 890775Notes

Reaction equation

HRID 890775 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][N:16]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[S:17]([CH3:20])(=[O:19])=[O:18])[CH:9]=1)(C)(C)C>Cl.O1CCOCC1>[Cl:30][C:26]1[CH:25]=[C:24]([CH2:23][CH2:22][CH2:21][N:16]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH2:14][C:10]2[CH:9]=[C:8]([CH2:7][C:6]([OH:31])=[O:5])[CH:13]=[CH:12][CH:11]=2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 1

HCID 53697450HCID 53697450, compound

Product 1

HCID 22246720HCID 22246720, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of [3-(2-{[3-(3-chloro-phenyl)-propyl]-methanesulfonyl-amino}ethyl)-phenyl]-acetic acid tert-butyl ester (170 mg, 0.36 mmol) in HCl/dioxane (5 mL) was stirred for 48 h at room temperature. The reaction was concentrated and the residue was taken up in dilute aqueous NaOH (10 mL, pH=9.3). The aqueous solution was washed with EtOAc (10 mL) and the layers were separated. The aqueous layer after extraction with EtOAc (10 mL) was acidified with dilute aqueous HCl to a pH of 2.5. After extraction of the acidic aqueous layer with EtOAc (10 mL) the organic solution was dried over MgSO4, filtered, and concentrated to afford the title compound as an oil (20 mg). 1H NMR (400 MHz, CDCl3) δ 6.90–7.50 (m, 8H), 3.00–3.30 (m, 4H), 2.95 (s, 3H), 2.45–2.85 (m, 4H), 1.80 (m, 2H); MS 408 (M−1).

Workup

  1. concentrationThe reaction was concentrated
  2. washThe aqueous solution was washed with EtOAc (10 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer after extraction with EtOAc (10 mL)
  5. extractionAfter extraction of the acidic aqueous layer with EtOAc (10 mL) the organic solution
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-80fbb3371157468790ff7e3ed2c1f0b3
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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