Hydrochloric Acid → HCID 86590685, compound

HRID 1866148Notes

Reaction equation

HRID 1866148 reaction equation
C(OC([N:8]([CH2:32][C@@H:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=1)[OH:34])[CH2:9][CH2:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=2)[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:13][CH:12]=1)=O)(C)(C)C.Cl>O1CCCC1.O1CCOCC1>[Cl:41][C:37]1[CH:36]=[C:35]([C@@H:33]([OH:34])[CH2:32][NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:30][CH:31]=2)[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86590684HCID 86590684, compound

Product 1

HCID 86590685HCID 86590685, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl [3-[[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-amino]ethyl]phenoxy]methyl]phenoxy]acetate (1.0 g) in tetrahydrofuran (5.0 ml) was added 4N hydrochloride in dioxane (4.3 ml). The mixture was stirred at room temperature for 8 hours and evaporated under reduced pressure. The residue was diluted with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (methanol/chloroform=1/20) to give ethyl [3-[[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenoxy]-methyl]phenoxy]acetate (632 mg).

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (methanol/chloroform=1/20)

Sources & evidence

ORD record
ord-497947b4a6f54e908c304ab7b1d0491c
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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