Pyridine → HCID 58503128, 화합물

HRID 1949609

반응식

HRID 1949609 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@H:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CN(C1C=CN=CC=1)C>[C:25]([O:18][C@@H:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:15]([OH:17])=[O:16])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 2733930(S)-2-Hydroxy-4-(((phenylmethoxy)carbonyl)amino)butyric acid

생성물 1

HCID 58503128HCID 58503128, 화합물수율 51%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of (S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoic acid (1, 612 g, 2.41 mol) in THF (6 L) at 0° C. was added DMAP (2.4 g) and pyridine (196 mL, 2.41 mol). After stirring for 20 minutes, benzoyl chloride (280 mL) was added slowly and the reaction was allowed to stir overnight at room temperature. The resulting precipitate was filtered and the filtrate was acidified with 1 M citric acid (1 L). The organic solvent was removed by rotary evaporation and the desired product was extracted with EtOAc (2×2 L). The combined organic layers were washed with 1 M citric acid (1 L), brine (1 L) and then dried over MgSO4. Solvent removal under vacuum resulted in a viscous oil, which was purified on a 6-inch reverse-phase HPLC column to yield (S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid (2) as a non-flowing viscous oil (439 g, 51% yield).

후처리

  1. stirringto stir overnight at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customThe organic solvent was removed by rotary evaporation
  4. extractionthe desired product was extracted with EtOAc (2×2 L)
  5. washThe combined organic layers were washed with 1 M citric acid (1 L), brine (1 L)
  6. dry with materialdried over MgSO4
  7. customSolvent removal under vacuum
  8. customresulted in a viscous oil, which
  9. customwas purified on a 6-inch reverse-phase HPLC column

출처 및 근거

ORD 기록
ord-d93126a2f8ba42a28863f775dba045ff
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399419B2

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