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Methanesulfonic Acid → (4R,5S)-2-[5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-4,5-dimethyl-4,5-dihydro-1,3-oxazole

HRID 909626
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HRID 909626 반응식
[OH:1][C@H:2]([CH3:36])[C@H:3]([NH:5][C:6]([C:8]1[NH:9][C:10]([C:13]2[CH:18]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=[C:15]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:14]=2)=[CH:11][CH:12]=1)=O)[CH3:4].CS(O)(=O)=O.C(N(CC)CC)C.[Cl-].[NH4+]>O1CCCC1>[CH3:34][O:33][CH2:32][C@@H:31]([O:30][C:15]1[CH:14]=[C:13]([C:10]2[NH:9][C:8]([C:6]3[O:1][C@@H:2]([CH3:36])[C@@H:3]([CH3:4])[N:5]=3)=[CH:12][CH:11]=2)[CH:18]=[C:17]([O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:27]([CH3:29])[CH3:28])[CH:16]=1)[CH3:35]
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참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66681067N-[(2R,3R)-3-Hydroxybutan-2-yl]-5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrole-2-carboxamide

생성물 1

HCID 66683078(4R,5S)-2-[5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-4,5-dimethyl-4,5-dihydro-1,3-oxazole
수율 100.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-[(2R,3R)-3-Hydroxybutan-2-yl]-5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrole-2-carboxamide (722 mg, 1.39 mmol) synthesized in Example (109a) was dissolved in tetrahydrofuran (30 mL), and anhydrous methanesulfonic acid (430 mg, 2.47 mmol) and triethylamine (1.20 mL, 8.61 mmol) were added, and stirring was carried out at 50° C. overnight under nitrogen atmosphere. The reaction solution was brought back to room temperature, and a saturated aqueous ammonium chloride solution (50 mL) was added, followed by extraction with methylene chloride (50 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-70%) to afford the desired compound (700 mg, yield 100%) as a yellow liquid.

후처리

  1. customwas brought back to room temperature
  2. extractionfollowed by extraction with methylene chloride (50 mL)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-70%)

출처 및 근거

ORD 기록
ord-6172a7f32d39479a8faee27399bb67fb
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017610B2

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