Sodium Hydroxide → 4'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid

HRID 2078657Notes

Reaction equation

HRID 2078657 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=1)[OH:37])[CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=1)[OH:37])[CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67097299methyl 4'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylate

Product 1

HCID 670977074'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acidYield 100.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4′-[[2-[(tert-butoxycarbonyl)-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylate (125 mg) in methanol (1.750 ml) and tetrahydrofuran (0.900 ml) was added 1N aqueous sodium hydroxide solution (1.05 ml) and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added 1N aqueous sodium hydroxide solution (0.900 ml) and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and to the residue were added ethyl acetate (40 ml) and water (20 ml). The pH value was adjusted to 5.70 by addition of 0.1N hydrochloric acid and the separated organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation gave 4′-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid (123 mg) as a yellow foam.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  3. additionwere added ethyl acetate (40 ml) and water (20 ml)
  4. additionThe pH value was adjusted to 5.70 by addition of 0.1N hydrochloric acid
  5. washthe separated organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. customfollowed by evaporation

Sources & evidence

ORD record
ord-094d5326020f4171bbebe2714c6e39f2
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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