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4-Toluenesulfonyl chloride → (S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl 4-methylbenzenesulfonate

HRID 1046693
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HRID 1046693 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][O:10][S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:18])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

생성물 1

HCID 11069512(S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl 4-methylbenzenesulfonate수율 77%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

The recovered intermediate (20a) (8.5 g, 33 mmol, 1.0 eq) was dissolved into 70 mL pyridine containing potassium hydroxide (2.1 g, 37 mmol, 1.1 eq) and the mixture was chilled in an ice bath. Tosyl chloride (7.1 g, 37 mmol, 1.1 eq) was added and the mixture was stirred at 0° C. for 2 hours then refrigerated overnight. The mixture was filtered and the filtrate was concentrated under reduced pressure. The recovered residue was dissolved into 300 mL EtOAc, washed with 2×200 mL 1M H3 PO4, saturated bicarbonate, and saturated aqueous NaCl. The organic was dried over MgSO4 and concentrated under reduced pressure to yield intermediate (20b) (10.3 g) as a pale brown oil.

후처리

  1. temperaturethe mixture was chilled in an ice bath
  2. waitthen refrigerated overnight
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe recovered residue was dissolved into 300 mL EtOAc
  6. washwashed with 2×200 mL 1M H3 PO4, saturated bicarbonate, and saturated aqueous NaCl
  7. dry with materialThe organic was dried over MgSO4
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4b453c3d87954531872ed0ce9289c04e
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569351B2

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