4-Methylmorpholine → 2-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

HRID 2197270노트

반응식

HRID 2197270 반응식
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:52][C@H:53]([CH:58]([CH3:60])[CH3:59])[C:54]([O:56][CH3:57])=[O:55]>CN(C=O)C>[CH3:57][O:56][C:54](=[O:55])[CH:53]([NH:52][C:9](=[O:11])[CH:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:21][CH:20]=1)[CH:58]([CH3:60])[CH3:59]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11984198Methyl D-valinate hydrochlorideHCID 66660912HCID 66660912, 화합물2회

생성물 1

HCID 666609032-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
-15 °C

실험 절차

A solution of the compound obtained in step e above (22e) (816 mg, 2.27 mmol), NMM (0.55 mL, 4.922 mmol) and HOBt (521 mg, 3.864 mmol) in DMF (10 mL) was stirred at 0° C. for 10 minutes, then the reaction was cooled to −15° C., and EDCl (478 mg, 2.497 mmol) was added. The reaction was stirred for 30 minutes at −15° C. and then allowed to warm to room temperature, (R)-methyl 2-amino-3-methylbutanoate hydrochloride (417 mg, 2.497 mmol) was added. After being stirred overnight, the reaction mixture was concentrated under vacuum; the residue was diluted with EtOAc and washed with brine. The combined organic layers were dried and concentrated; the residue was purified by silica gel column chromatography to give the title compound as colourless oil (900 mg, 84%).

후처리

  1. temperatureto warm to room temperature
  2. stirringAfter being stirred overnight
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. additionthe residue was diluted with EtOAc
  5. washwashed with brine
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-51fdda5d35b14343bb07487f0c578983
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338471B2

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