Triphenylphosphine → (S)-N-(5-bromothiazol-2-yl)-N-(2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropyl)acetamide

HRID 661020

반응식

HRID 661020 반응식
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][CH:3]=1.O[CH2:12][C@@H:13]([N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[S:6][C:5]([N:7]([CH2:12][C@@H:13]([N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:8](=[O:10])[CH3:9])=[N:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 3502602-Acetamido-5-bromo-1,3-thiazoleHCID 5363146Diisopropyl azodicarboxylateHCID 11323487(2S)-2-Phthalimido-3-phenyl-propanol

생성물 1

HCID 57634091(S)-N-(5-bromothiazol-2-yl)-N-(2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropyl)acetamide수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

N-(5-Bromo-thiazol-2-yl)-acetamide) (442.0 mg, 2.0 mmol), (S)-2-(1-hydroxy-3-phenylpropan-2-yl)isoindoline-1,3-dione (281.0 mg, 1.0 mmol), triphenylphosphine (303.0 mg, 1.5 mmol) and THF (15.0 mL) were charged into a 100 mL round bottom flask. The resulting reaction mixture was a suspension. The flask was immersed in an ice-water bath. After stirring for 15 minutes under nitrogen, a solution of DIAD (421.5 mg, 1.5 mmol) in 3.0 mL THF was slowly added to the flask through a syringe. The reaction mixture became a clear solution after the addition was complete. After 10 minutes, the reaction mixture was brought to room temperature by removing the ice water bath and the stirring was continued for 16 hours. THF was evaporated off, and the residue was diluted with 40 mL saturated sodium bicarbonate and extracted with DCM (75 mL×2). The residue was subjected to a silica gel column chromatography purification with hexane-EtOAc (7:3) as the eluant to afford a compound as a white solid (S)—N-(5-bromothiazol-2-yl)-N-(2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropyl)acetamide (20 mg, yield 17%). LCMS (API-ES) m/z (%): 484.0 (100%, M++H).

후처리

  1. customThe resulting reaction mixture
  2. customThe flask was immersed in an ice-water bath
  3. additionafter the addition
  4. waitAfter 10 minutes
  5. customwas brought to room temperature
  6. customby removing the ice water bath
  7. waitthe stirring was continued for 16 hours
  8. customTHF was evaporated off
  9. additionthe residue was diluted with 40 mL saturated sodium bicarbonate
  10. extractionextracted with DCM (75 mL×2)
  11. customThe residue was subjected to a silica gel column chromatography purification with hexane-EtOAc (7:3) as the eluant

출처 및 근거

ORD 기록
ord-33c5b80b515744958f992779108366ad
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084479B2

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