Water → 5-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

HRID 412494노트

반응식

HRID 412494 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36][C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:32]([F:56])[CH:31]=2)[CH2:25]1)=[N+]=[N-].O.[C:58](OC(=O)C)(=[O:60])[CH3:59].N1C=CC=CC=1>C1COCC1>[C:58]([NH:20][CH2:23][C@@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36][C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:32]([F:56])[CH:31]=2)[CH2:25]1)(=[O:60])[CH3:59]

참가 물질

7

반응물 5

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11776TriphenylphosphineHCID 229662215-(S)-azidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

생성물 1

HCID 229661975-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphenylphosphine (2.82 g, 10.8 mmol) was added portionwise to a solution of 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]-oxazolidine-2-one (5.00 g, 9.79 mmol) in THF (40 mL), and the mixture stirred for 2 h at room temperature. Water (1.41 mL, 78.3 mmol) was added, and the mixture heated at 40° C. overnight. Solvent was removed under vacuum, and the oily residue dissolved in dichloromethane (50 mL). Acetic anhydride (4.62 ml, 49.0 mmol) and pyridine (7.92 ml, 97.9 mmol) were added, and the mixture stirred for 8 h at r.t. Solvent was removed under vacuum and the crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes) to give the product as a foam (4.98 g, 97%); MS: 527 [M+H]+. 1H NMR.

후처리

  1. temperaturethe mixture heated at 40° C. overnight
  2. customSolvent was removed under vacuum
  3. dissolutionthe oily residue dissolved in dichloromethane (50 mL)
  4. stirringthe mixture stirred for 8 h at r.t
  5. customSolvent was removed under vacuum
  6. customthe crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-a44d89b1243542459217e0f4ecbcc157
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562844B2

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