Hydrochloric Acid → HCID 24824639, compound

HRID 1866187Notes

Reaction equation

HRID 1866187 reaction equation
C(OC([N:8]([CH2:19][CH2:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][C:26]2[CH:40]=[CH:39][C:29]([O:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[OH:11])=O)(C)(C)C.Cl.O1CCCC1>O1CCOCC1>[ClH:18].[Cl:18][C:14]1[CH:13]=[C:12]([C@@H:10]([OH:11])[CH2:9][NH:8][CH2:19][CH2:20][C:21]2[CH:42]=[CH:41][C:24]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:39][CH:40]=3)=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 24824078HCID 24824078, compound

Product 1

HCID 24824639HCID 24824639, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl [4-[4-[2-[N-(tert-butoxycarbonyl)-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-amino]ethyl]benzyl]phenoxy]acetate (240 mg) and 4N hydrochloride in 1,4-dioxane (3.0 ml) was stirred at room temperature for 24 hours. The mixture was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (methanol/acetic acid/chloroform=10/1/100) to give a product. To a tetrahydrofuran (2.0 ml) solution of the product, 4N hydrogen chloride in 1,4-dioxane (1.0 ml) was added. The mixture was stirred for 5 minutes and evaporated under reduced pressure to give [4-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]benzyl]phenoxy]acetic acid hydrochloride (72 mg).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (methanol/acetic acid/chloroform=10/1/100)
  3. customto give a product
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2ba0b85311f742c5a97a34d536e71e11
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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