Triphenylphosphine → (S)-2-tert-Butoxycarbonylamino-3-(2-chloro-6-nitro-phenoxy)-propionic acid benzyl ester

HRID 1348589

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HRID 1348589 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[C:34]=1[OH:42].[CH2:43]([O:50][C:51](=[O:63])[C@@H:52]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:53]O)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[CH2:43]([O:50][C:51](=[O:63])[C@@H:52]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:53][O:42][C:34]1[C:35]([N+:39]([O-:41])=[O:40])=[CH:36][CH:37]=[CH:38][C:33]=1[Cl:32])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 11784Phenol, 2-chloro-6-nitro-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7018792Boc-Ser-OBzl

생성물 1

HCID 67076911(S)-2-tert-Butoxycarbonylamino-3-(2-chloro-6-nitro-phenoxy)-propionic acid benzyl ester수율 50.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Under an inert atmosphere, a solution of 6.5 g (25 mmol) of triphenylphosphine in 20 ml of tetrahydrofurane was treated with at 0° C. with 3.9 ml (25 mmol) of diethyl azodicarboxylate. Thereupon, 3.0 g (17 mmol) of 2-chloro-6-nitrophenol were added and the reaction mixture was stirred at 0° C. for 15 minutes. Finally, 4.93 g (17 mmol) of (S)-2-tert-butoxycarbonylamino-3-hydroxy-propionic acid benzyl ester were added and the reaction mixture was left to warm to room temperature. After stirring for 18 hours, for the working-up the solvent was evaporated under reduced pressure and the residue triturated in ether at 0° C. The precipitated triphenylphosphinoxide was filtered and washed with ether. The combined filtrates were evaporated to yield 12.8 g of the crude product as a brown-yellow oil. The crude product was purified by chromatography on silica gel using heptane and ethyl acetate as the eluent. There were obtained 3.9 g (50%) of the title compound as a yellow oil, [α]589=−5.96° (c=1.0% in MeOH), MS m/e (%): 468.1 (M+NH4+, 100).

후처리

  1. waitthe reaction mixture was left
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for 18 hours
  4. customwas evaporated under reduced pressure
  5. customthe residue triturated in ether at 0° C
  6. filtrationThe precipitated triphenylphosphinoxide was filtered
  7. washwashed with ether
  8. customThe combined filtrates were evaporated
  9. customto yield 12.8 g of the crude product as a brown-yellow oil
  10. customThe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-869dac237d604566ac448f3c86457951
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211573B2

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