Hydrochloric Acid → HCID 11114462, compound

HRID 398199Notes

Reaction equation

HRID 398199 reaction equation
C([O:3][C:4](=[O:46])[CH:5]([N:24]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)=[O:26])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19]([O:21]CC)=[O:20])([CH3:18])[CH3:17])=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>O1CCOCC1>[CH2:39]([N:24]([C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)=[O:26])[CH:5]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19]([OH:21])=[O:20])([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[C:4]([OH:46])=[O:3])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69871072HCID 69871072, compound

Product 1

HCID 11114462HCID 11114462, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A sample of 2-[benzyl-(biphenyl-4-carbonyl)-amino]-4-[4-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenoxy]-butyric acid ethyl ester (687 mg, 1.10 mmol) was dissolved in 5 mL of dioxane followed by addition of 5.0 N NaOH (2.3 mL, 11.6 mmol). The mixture was magnetically stirred and heated at 60° C. for 7 hours. The reaction mixture was allowed to cool to room temperature followed by addition of 1.0 N HCl (12 mL, 12 mmol) then partitioned by addition of methylene chloride (50 mL). The organic phase was separated, dried over sodium chloride and concentrated under reduced pressure to yield 690 mg (≈100%) of a glassy solid. HPLC RT1=2.24 min; 1H NMR (400 MHz, CDCl3) δ12.82 (broad s, 2H), 7.70-7.75 (m, 4H), 7.45-7.17 (m, 10H), 6.75-6.48 (m, 4H), 2.24-2.00 (m, 2H), 1.39 (s, 6H); MS (EI) 568.31 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. customthen partitioned by addition of methylene chloride (50 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium chloride
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0e8a391c7cf4009974853b3c5a1a9ae
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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