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Triethylamine → (2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidin

HRID 1720530
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HRID 1720530 반응식
C(O[C:6]([N:8]1[CH2:29][CH2:28][CH2:27][C@H:9]1[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH:17]([OH:26])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:11])=[O:7])(C)(C)C.C(N(CC)CC)C.[O:37]([CH2:44]C(Cl)=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>Cl.O1CCOCC1.C(Cl)Cl>[OH:26][CH:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:10](=[O:11])[C@@H:9]1[CH2:27][CH2:28][CH2:29][N:8]1[C:6](=[O:7])[CH2:44][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 70050944(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine

생성물 1

HCID 67771420(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidin

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 20443148
1,4-Dioxane hydrochloride
용매

실험 절차

(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (996 mg) was dissolved in 4N hydrochloric acid/1,4-dioxane (12 ml), and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was concentrated to dryness, and the residue obtained was dissolved in methylene chloride (10 ml). After triethylamine (0.68 ml) was added thereto under ice-cooling, phenoxyacetyl chloride (0.34 ml) was dropwise added. After stirring the mixture under ice-cooling for 0.5 hour, and then at room temperature for 1.5 hours, the reaction mixture was poured into ice-water, and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 1.05 g of the title compound.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue obtained
  3. temperatureunder ice-cooling
  4. stirringAfter stirring the mixture under ice-
  5. temperaturecooling for 0.5 hour
  6. waitat room temperature for 1.5 hours
  7. extractionextracted with methylene chloride
  8. washThe organic layer was washed with saturated aqueous sodium bicarbonate, and saturated brine successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

출처 및 근거

ORD 기록
ord-d29c441a9b4a44b293dde11d5097ffea
출처 데이터셋
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05506256

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