Acetic Acid → (R)-4-Benzyl-3-((S)-2-(4-fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-butyryl)-oxazolidin-2-one

HRID 1158145Notes

Reaction equation

HRID 1158145 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:29])[C@H:15]([CH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([F:27])=[C:22]([CH3:28])[CH:21]=1)[CH2:16]C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][NH:40][CH3:41])=[CH:33][CH:32]=1.[C:42](O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:29])[C@@H:15]([CH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([F:27])=[C:22]([CH3:28])[CH:21]=1)[CH2:16][CH2:41][N:40]([CH2:39][CH2:38][CH2:37][C:34]1[CH:33]=[CH:32][C:31]([F:30])=[CH:36][CH:35]=1)[CH3:42])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 110842664-Fluoro-N-methyl-benzenepropanamineHCID 59512579(R)-4-Benzyl-3-[(S)-2-(4-fluoro-3,5-dimethyl-benzyl)-pent-4-enoyl]-oxazolidin-2-one

Product 1

HCID 68642196(R)-4-Benzyl-3-((S)-2-(4-fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-butyryl)-oxazolidin-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (R)-4-benzyl-3-[(S)-2-(4-fluoro-3,5-dimethyl-benzyl)-pent-4-enoyl]-oxazolidin-2-one (0.045 g, 0.113 mmol), [3-(4-fluoro-phenyl)-propyl]-methyl-amine (C6, 0.023 g, 0.136 mmol), and acetic acid (0.014 g, 0.226 mmol) in 3 mL of dichloroethane, was added NaBH(OAc)3 (0.034 g, 0.158 mmol). After stirring at room temperature overnight, the reaction was quenched with 20 mL of saturated aqueous NaHCO3 solution and the reaction mixture extracted with ethyl acetate (20 mL×3). The combined organic extracts were dried, filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel) eluting with 0-10% methanol/dichloromethane to give the title compound as colorless oil (0.046 g, 75% yield). LC-MS: tR=7.7 min; m/z 549 (M+H)+.

Workup

  1. customthe reaction was quenched with 20 mL of saturated aqueous NaHCO3 solution
  2. extractionthe reaction mixture extracted with ethyl acetate (20 mL×3)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was isolated by Flash column chromatography (silica gel)
  7. washeluting with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-821574373583487ab0e438755d6edd68
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

Loading…