Sodium Hydroxide → 4'-[[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-amino]-N-[(3-hydroxypropyl)sulfonyl]-3-isobutoxy-4-biphenylcarboxamide dihydrochloride

HRID 2078670Notes

Reaction equation

HRID 2078670 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][S:8]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][C@@H:31]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[OH:32])=[CH:22][CH:21]=2)=[CH:16][C:15]=1[O:47][CH2:48][CH:49]([CH3:51])[CH3:50])=[O:13])(=[O:10])=[O:9])(=O)C.[OH-].[Na+]>CO.O1CCCC1>[ClH:39].[ClH:39].[Cl:39][C:35]1[CH:34]=[C:33]([C@@H:31]([OH:32])[CH2:30][NH:29][CH2:28][CH2:27][NH:26][C:23]2[CH:22]=[CH:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([C:12]([NH:11][S:8]([CH2:7][CH2:6][CH2:5][OH:4])(=[O:10])=[O:9])=[O:13])=[C:15]([O:47][CH2:48][CH:49]([CH3:50])[CH3:51])[CH:16]=3)=[CH:25][CH:24]=2)[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 670975243-[[[[4'-[[2-[(tert-butoxycarbonyl)-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-isobutoxy-4-biphenylyl]carbonyl]amino]sulfonyl]propyl acetate

Product 1

HCID 670981934'-[[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-amino]-N-[(3-hydroxypropyl)sulfonyl]-3-isobutoxy-4-biphenylcarboxamide dihydrochlorideYield 241.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[[[4′-[[2-[(tert-butoxycarbonyl)-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-isobutoxy-4-biphenylyl]carbonyl]amino]sulfonyl]propyl acetate (34.0 mg) in methanol (0.340 ml) and tetrahydrofuran (0.170 ml) was added 1N aqueous sodium hydroxide solution (0.228 ml) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate, washed with water and brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure. To a solution of the resulting residue in 1,4-dioxane (0.340 ml) was added 4N hydrogen chloride in 1,4-dioxane (0.340 ml) and the mixture was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and to the residue was added ethyl acetate. The precipitate was collected by filtration and dried in vacuo to give 4′-[[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-N-[(3-hydroxypropyl)sulfonyl]-3-isobutoxy-4-biphenylcarboxamide dihydrochloride (24.8 mg) as a yellow powder.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. additionTo a solution of the resulting residue in 1,4-dioxane (0.340 ml) was added 4N hydrogen chloride in 1,4-dioxane (0.340 ml)
  6. stirringthe mixture was stirred at room temperature overnight
  7. concentrationThe solvent was concentrated under reduced pressure and to the residue
  8. additionwas added ethyl acetate
  9. filtrationThe precipitate was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4fde6245fd5f49d7802cebe4cc6a6afb
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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