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 1158145ノート

反応式

HRID 1158145 の反応式
[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

参加物

6

反応物 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

生成物 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-one収率 75%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-821574373583487ab0e438755d6edd68
出典データセット
uspto-grants-2010_10
特許番号
US07807720B2

反応ノート

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