Sodium Hydroxide → (3-{3-[(4-Fluoro-3-methyl-benzyl)-((R)-2-phenyl-propyl)-amino]-propoxy}-phenyl)-acetic Acid

HRID 902627Notes

Reaction equation

HRID 902627 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH:6]=1.[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=1[CH3:35].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O.C(O)(=O)C>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:15]([CH2:16][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:25])[CH:10]=[CH:9][CH:8]=2)=[CH:29][C:28]=1[CH3:35]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 27348744-Fluoro-3-methylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69253831HCID 69253831, compound

Product 1

HCID 59701434(3-{3-[(4-Fluoro-3-methyl-benzyl)-((R)-2-phenyl-propyl)-amino]-propoxy}-phenyl)-acetic AcidYield 54%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of {3-[3-((R)-2-Phenyl-propylamino)-propoxy]-phenyl}-acetic acid methyl ester (100 mg, 293 mmol) in methanol (1 ml) was added acetic acid (10% by volume) followed by 4-Fluoro-3-methyl-benzaldehyde (121 mg, 879 mmol) and sodium cyanoborohydride (54.5 mg, 879 mmol). After the resulting mixture was stirred for 18 h at RT water was added to quench the reaction. The solution was made basic by the addition of sodium hydroxide and heated for 30 min. The sample concentrated in vacuo and purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: 0.1% trifluoroacetic acid in acetonitrile B: 0.1% aqueous trifluoroacetic acid, A: 10 to 90% during 10 min, UV detection at 254 nm) to give the title compound as a solid (71.6 mg, 54%). MS (ESI) 450.0 (M+H)+.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. temperatureheated for 30 min
  5. concentrationThe sample concentrated in vacuo
  6. custompurified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-b87fa3aafecd402fbfb48da1d780ad37
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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