Ammonium Acetate → HCID 54187452, 화합물

HRID 480195

반응식

HRID 480195 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:36].[Na+]>CO>[NH2:36][CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C:12]([N:14]1[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13]

참가 물질

5

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

생성물 1

HCID 54187452HCID 54187452, 화합물수율 99.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (1.86 g, 4.44 mmol) in MeOH (20 mL) was added ammonium acetate (3.42 g, 44 mmol) and sodium cyanoborohydride (0.195 g, 3.1 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was quenched with concentrated hydrochloric acid and concentrated in vacuo. The residue was dissolved in water and basified with aqueous 3N NaOH (pH>10). The product was extracted with dichloromethane (2×) and ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.29 g, 69% yield)

후처리

  1. customThe reaction was quenched with concentrated hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water and basified with aqueous 3N NaOH (pH>10)
  4. extractionThe product was extracted with dichloromethane (2×) and ethyl acetate (2×)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c4ef7363554341ffa01d88267800552d
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649611B2

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