4-Methylmorpholine → HCID 86621120, 화합물

HRID 601718노트

반응식

HRID 601718 반응식
C(N1[C@H:12]([CH3:13])[C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)OC1=O)(=O)CCCCC.Cl.[CH2:22]([O:24][C:25](=[O:36])[C@H:26]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:27])[CH3:23].CN(C([O:44]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH2:11]([C@H:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:19]([NH:27][C@@H:26]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25]([O:24][CH2:22][CH3:23])=[O:36])=[O:44])[CH:12]=[CH2:13]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2734606(S)-ethyl 2-amino-4-phenylbutanoate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10858719HCID 10858719, 화합물

생성물 1

HCID 86621120HCID 86621120, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the compound of step G (3) (421 mg, 2.69 mmol) and homophenylalanine ethyl ester hydrochloride (789 mg, 3.24 mmol) in DMF (30.1 mL) was added HATU (1.54 g, 3.24 mmol) and N-Methyl morpholine (1.24 mL, 9.42 mmol). The reaction was stirred at rt until LC showed conversion to product (<30 min). DMF was removed in vacuo, the residue suspended in water, and the product extracted 3 times to ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was suspended in a minimal amount of methylene chloride and filtered through glass wool. The solution was loaded onto a silica gel column, and pure product was obtained following elution with a ethyl acetate/hexane gradient (836 mg, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 0.88 (t, J=7.02 Hz, 3H) 1.19-1.38 (m, 7H) 1.40-1.50 (m, 1H) 1.57-1.69 (m, 1H) 1.92-2.06 (m, 1H) 2.08-2.26 (m, 3H) 2.28-2.41 (m, 1H) 2.52-2.75 (m, 2H) 4.18 (q, J=7.32 Hz, 2H) 4.61-4.74 (m, 1H) 4.95-5.11 (m, 2H) 5.69-5.84 (m, 1H) 5.96 (d, J=7.63 Hz, 1H) 7.10-7.34 (m, 5H). HPLC retention time: 1.76 min (method A). MS (ESI) (M+H)+ 346.

후처리

  1. customto product (<30 min)
  2. customDMF was removed in vacuo
  3. extractionthe product extracted 3 times to ethyl acetate
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered through glass wool
  8. custompure product was obtained
  9. washelution with a ethyl acetate/hexane gradient (836 mg, 90%)

출처 및 근거

ORD 기록
ord-380d73af2f3a431c9f55b02f3cdc5c64
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902218B2

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