Hydrochloric Acid → HCID 23087471, compound

HRID 1950328Notes

Reaction equation

HRID 1950328 reaction equation
C(N(C1C=C(OC)C=CC=1C1CCC2C(=CC=C(OC)C=2)C1)C(=O)C1C=CC(O)=CC=1)C.ClCC(OCC)=O.C([O:42][C:43](=[O:77])[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([C:52](=[O:76])[N:53]([CH2:74][CH3:75])[C:54]2[CH:59]=[C:58]([O:60][CH3:61])[CH:57]=[CH:56][C:55]=2[CH:62]2[CH2:71][CH2:70][C:69]3[C:64](=[CH:65][CH:66]=[C:67]([O:72][CH3:73])[CH:68]=3)[CH2:63]2)=[CH:48][CH:47]=1)C.[OH-].[Na+].Cl>O1CCCC1.O>[CH2:74]([N:53]([C:54]1[CH:59]=[C:58]([O:60][CH3:61])[CH:57]=[CH:56][C:55]=1[CH:62]1[CH2:71][CH2:70][C:69]2[C:64](=[CH:65][CH:66]=[C:67]([O:72][CH3:73])[CH:68]=2)[CH2:63]1)[C:52]([C:49]1[CH:48]=[CH:47][C:46]([O:45][CH2:44][C:43]([OH:77])=[O:42])=[CH:51][CH:50]=1)=[O:76])[CH3:75]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 14798Sodium HydroxideHCID 57934373HCID 57934373, compoundHCID 66627175HCID 66627175, compound

Product 1

HCID 23087471HCID 23087471, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized from N-ethyl-4-hydroxy-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]benzamide and ethyl chloroacetate according to an analogous synthetic method to Preparation Example 40, to a solution of the resulting {4-{ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]carbamoyl}phenoxy}acetic acid ethyl ester (275 mg) in tetrahydrofuran (5 ml) was added an aqueous solution of 1N sodium hydroxide (5 ml) on an ice bath. The solution was stirred for 1.5 hours while warming to room temperature, then the reaction solution was acidified with 2N hydrochloric acid on the ice bath. Water was added thereto, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to provide the title compound (246 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washsequentially washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5b4d4efb9e2f457db993a17d7bd9a955
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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