Hydrochloric Acid → HCID 11114462, compound

HRID 2417122Notes

Reaction equation

HRID 2417122 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) δ 12.82 (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-a13a1fb408df478eab31f264a66b5886
Source dataset
uspto-grants-2004_11
Patent number
US06825222B2

Reaction notes

Loading…