Triphenylphosphine → (R)-tert-butyl 4-((1R,2S)-3-azido-1-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 924425노트

반응식

HRID 924425 반응식
C1C=CC(OP(OC2C=CC=CC=2)([N:10]=[N+:11]=[N-:12])=O)=CC=1.[Si:20]([O:27][C@@H:28]([C@H:33]1[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[N:34]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:29]([CH3:32])[CH2:30]O)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[N:10]([CH2:30][C@H:29]([CH3:32])[C@H:28]([C@H:33]1[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[N:34]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[O:27][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[N+:11]=[N-:12]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 123414Diphenylphosphoryl azideHCID 59226545(R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 59226479(R)-tert-butyl 4-((1R,2S)-3-azido-1-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diphenylphosphonic azide (1.3 mL, 5.9 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2-methylpropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.2 g, 3.0 mmol), diisopropyl azodicarboxylate (1.2 mL, 5.9 mmol) and PPh3 (1.6 g, 5.9 mmol) in THF (20 mL). The mixture was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-15% EtOAc in hexanes) to provide the sub-title compound (1.09 g, 86%). LCMS calc. for C15H33N4O2Si (M+H-Boc)+: m/z=329.2. found 329.2.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel (eluting with 0-15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-643c7aa088d5407bb42324435f93d37f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

반응 노트

불러오는 중…