Acetic Acid → (3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic Acid Methyl Ester

HRID 902673Notes

Reaction equation

HRID 902673 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([NH:16][CH2:17][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH3:15])[CH:6]=1.C(O)(=O)C.[Cl:31][C:32]1[C:39]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CCCCCC.O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([N:16]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[C:39]([C:40]([F:41])([F:43])[F:42])[C:32]=2[Cl:31])[CH2:17][C@H:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19])[CH3:15])[CH:6]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69254631{3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl Ester

Product 1

HCID 69252464(3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic Acid Methyl EsterYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of {3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic acid methyl ester (0.12 g, 0.34 mmol) in dry dichloromethane was added acetic acid followed by 2-chloro-3-trifluoromethylbenzaldehyde (0.1 g, 0.51 mmol) and sodium triacetoxyborohydride (0.149, 0.68 mmol). After the resulting mixture was stirred at room temperature overnight water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by silica gel column chromatography using EtOAc:Hexane/25:75 as the eluent to give 50 mg (40% yield) of the title compound as an oil MS m/e 548.4 (M+H)+.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacco
  8. customThe crude mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc3d50e37c0643dda69ba45a1376ddda
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…