Hydrochloric Acid → 4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)butyric Acid

HRID 1039807Notes

Reaction equation

HRID 1039807 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][NH:7][CH2:8][C:9](=[O:34])[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1.[OH-].[Na+].Cl>C1COCC1>[C:22]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:19]([O:18][CH:15]1[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][C:9]([CH2:8][NH:7][CH2:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:34])[CH2:17][CH2:16]1)=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 667817944-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)butyric acid methyl ester

Product 1

HCID 667816914-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)butyric Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)butyric acid methyl ester (1.00 g, 2.08 mmol) in THF (10 mL) was added dropwise aqueous sodium hydroxide (1.0 M, 10.4 mL, 10.4 mmol) and the reaction mixture was stirred overnight at room temperature. LC-MS (Method 10-90) showed product was present (Rt 3.34 min; m/z 468.2 [M+H]+). The pH of the mixture was adjusted to pH 5 with aqueous hydrochloric acid (6 M) and the mixture was concentrated under reduced pressure. Aqueous ammonium chloride solution was added to the residue and this mixture was washed with EtOAc. The pH of the aqueous layer was adjusted to pH 4 with phosphate buffer solution and the aqueous layer was then extracted with a 1:3 mixture of isopropyl acetate/chloroform (4×). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as a colorless oil, which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionAqueous ammonium chloride solution was added to the residue
  3. washthis mixture was washed with EtOAc
  4. extractionthe aqueous layer was then extracted with a 1:3 mixture of isopropyl acetate/chloroform (4×)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73ec858a7b6d4590a31191651c6ff6c1
Source dataset
uspto-grants-2013_10
Patent number
US08551978B2

Reaction notes

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