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

HRID 909632노트

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HRID 909632 반응식
[OH:1][C@H:2]([CH3:47])[C@H:3]([NH:16][C:17]([C:19]1[NH:20][C:21]([C:24]2[CH:29]=[C:28]([O:30][Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])[CH:27]=[C:26]([O:41][C@@H:42]([CH3:46])[CH2:43][O:44][CH3:45])[CH:25]=2)=[CH:22][CH:23]=1)=O)[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].CS(O)(=O)=O.C(N(CC)CC)C.[Cl-].[NH4+]>O1CCCC1>[CH3:45][O:44][CH2:43][C@@H:42]([O:41][C:26]1[CH:25]=[C:24]([C:21]2[NH:20][C:19]([C:17]3[O:1][C@@H:2]([CH3:47])[C@@H:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:7]([CH3:9])[CH3:8])[CH:10]([CH3:11])[CH3:12])[N:16]=3)=[CH:23][CH:22]=2)[CH:29]=[C:28]([O:30][Si:31]([CH:32]([CH3:34])[CH3:33])([CH:35]([CH3:36])[CH3:37])[CH:38]([CH3:40])[CH3:39])[CH:27]=1)[CH3:46]

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66683504N-{(2R,3R)-3-Hydroxy-1-[(tripropan-2-ylsilyl)oxy]butan-2-yl}-5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrole-2-carboxamide

생성물 1

HCID 66890739(4R,5S)-2-[5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-5-methyl-4-{[(tripropan-2-ylsilyl)oxy]methyl}-4,5-dihydro-1,3-oxazole수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

N-{(2R,3R)-3-Hydroxy-1-[(tripropan-2-ylsilyl)oxy]butan-2-yl}-5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrole-2-carboxamide (2.52 g, 3.65 mmol) synthesized in Example (110b) was dissolved in tetrahydrofuran (20 mL), and anhydrous methanesulfonic acid (1.05 g, 6.03 mmol) and triethylamine (2.00 mL, 14.35 mmol) were added, followed by stirring at 50° C. for 1 day under nitrogen atmosphere. To the reaction solution, a saturated aqueous ammonium chloride solution (50 mL) was added, and extraction was carried out 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=10%-30%) to afford the desired compound (2.30 g, yield 94%) as a pale yellow liquid.

후처리

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-30%)

출처 및 근거

ORD 기록
ord-be24d44e759a4550b94fe4d0303cce45
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017610B2

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