Hydrochloric Acid → HCID 9820676, compound

HRID 890723Notes

Reaction equation

HRID 890723 reaction equation
[CH2:1]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:26][CH:27]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12150841HCID 12150841, compound

Product 1

HCID 9820676HCID 9820676, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Step A (379 mg, 0.95 mmol) in MeOH (6 mL) was added NaOH (1.0 mL, 5N). The reaction was stirred at room temperature for 24 h and was acidified with aqueous HCl (1N). The MeOH was removed in vacuo and the residue was dissolved in CH2Cl2. The organic solution was washed sequentially with HCl (1N, 1×), water (2×), and brine (1×). The organic solution was dried with MgSO4, filtered, and concentrated in vacuo. Purification by radial chromatography (CH2Cl2 to 6% MeOH/CH2Cl2) provided the title compound (356 mg). 1H NMR (400 MHz, CDCl3) δ 7.30–7.12 (m, 4H), 4.35 (s, 2H), 3.10–3.19 (m, 2H), 2.80 (s, 3H), 2.60 (t, 2H), 2.31 (t, 2H), 1.48–1.65 (m, 7H), 1.20–1.40 (m, 6H). 0.97 (t, 3H); MS 387 (M+18).

Workup

  1. customThe MeOH was removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organic solution was washed sequentially with HCl (1N, 1×), water (2×), and brine (1×)
  4. dry with materialThe organic solution was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by radial chromatography (CH2Cl2 to 6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-da67c76fa9fa48348c48c50f191dc66f
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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