4-Methylmorpholine → (2S)-2-[(2R)-(2-Tert-Butoxycarbonylamino-Propionyl)-(4-Fluoro-Benzyl)-Amino]propionic Acid Methyl Ester

HRID 11606

반응식

HRID 11606 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:29][O:30][C:31](=[O:43])[C@@H:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[CH3:33]>O1CCCC1>[CH3:29][O:30][C:31](=[O:43])[C@@H:32]([N:34]([C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:13])[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=1)[CH3:33]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 637606BOC-D-alanineHCID 43230250(S)-2-(4-fluoro-benzylamino)-propionic acid methyl ester

생성물 1

HCID 57016912(2S)-2-[(2R)-(2-Tert-Butoxycarbonylamino-Propionyl)-(4-Fluoro-Benzyl)-Amino]propionic Acid Methyl Ester수율 69.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-2-tert-butoxycarbonylamino-propionic acid (37 g, 195 mmol) in dry tetrahydrofuran (250 mL) at 0° C. was added 4-methyl morpholine (21.5 mL, 195 mmol) followed by isobutylchloroformate (25.3 mL, 195 mmol). The reaction was allowed to warm to ambient temperature and stirred for two hours. This was followed by the addition of (S)-2-(4-fluoro-benzylamino)-propionic acid methyl ester (34.4 g, 162 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate. The filtrate was concentrated in vacuo, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (43.2 g).

후처리

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe filter cake was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. additiondiluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c3814d07017d476faad65d26565c6cf8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

연결된 노트

불러오는 중…