Hydrochloric Acid → (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenylamino)-acetic Acid Hydrochloride

HRID 902708Notes

Reaction equation

HRID 902708 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[C:33]=2[Cl:42])[CH2:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[ClH:42].[Cl:42][C:33]1[C:34]([C:38]([F:39])([F:40])[F:41])=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][N:16]([CH2:17][CH:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:15][CH2:14][CH2:13][O:12][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][C:3]([OH:43])=[O:2])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69253762(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}phenylamino)-acetic acid methyl ester

Product 1

HCID 69253220(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenylamino)-acetic Acid Hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenylamino)-acetic acid methyl ester in THF (6 ml) and water (2 ml) was added lithium hydroxide monohydrate (20 mg, 0.47 mmol) and the mixture was stirred at room temperature for 6 hours. The reaction mixture was acidified with 1 M aqueous HCl (0.5 mL). The aqueous mixture was concentrated in vacuo and the crude material was dissolved in EtOAc. The ethyl acetate solution was washed with brine (1×), dried over sodium sulfate, and filtered. The organic layer was concentrated, and the crude amine was treated with 1 M HCl (Et2O). The resulting precipitate was dried under vacuum to afford the title compound as a solid. MS(ES) m/e 597.4 (M+).

Workup

  1. concentrationThe aqueous mixture was concentrated in vacuo
  2. dissolutionthe crude material was dissolved in EtOAc
  3. washThe ethyl acetate solution was washed with brine (1×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe organic layer was concentrated
  7. additionthe crude amine was treated with 1 M HCl (Et2O)
  8. customThe resulting precipitate was dried under vacuum

Sources & evidence

ORD record
ord-4dc0ffc30f494fd18d301eca300a109b
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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