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

HRID 924425ノート

反応式

HRID 924425 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-643c7aa088d5407bb42324435f93d37f
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

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