Triphenylphosphine → HCID 86726822, compound

HRID 1499603Notes

Reaction equation

HRID 1499603 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:10]([CH:13]1[CH2:15][CH2:14]1)[CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].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.C1C=CC(OP(OC2C=CC=CC=2)([N:72]=[N+:73]=[N-:74])=O)=CC=1>C1COCC1>[N:72]([CH2:11][C@H:10]([CH:13]1[CH2:15][CH2:14]1)[C@H:9]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:73]=[N-:74]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 5363146Diisopropyl azodicarboxylateHCID 86726819HCID 86726819, compound

Product 1

HCID 86726822HCID 86726822, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (4R)-4-((1R,2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropyl-3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.3 g, 3.0 mmol) and triphenylphosphine (1.6 g, 6.1 mmol) in anhydrous THF (20 mL), DIAD (1.2 mL, 5.9 mmol) was added drop-wise under an atmosphere of nitrogen. Upon completion of addition, a precipitate was formed. The reaction mixture was stirred for 30 min. then diphenylphosphonic azide (1.3 mL, 6.2 mmol) in anhydrous THF (1.0 mL) was added. After stirring at ambient temperature for 3 h, the volatile organic solvents were removed under reduced pressure and the crude product was purified by flash column chromatography (120 g of silica gel, eluting with 0-15% EtOAc-hexanes) to afford the sub-title compound as a light yellow oil (1.18 g, 86%). LC/MS (ESI) m/z calc. for C17H35N4O2Si: 355.30 [M-Boc+H]+. found: 355.1.

Workup

  1. additionUpon completion of addition
  2. customa precipitate was formed
  3. stirringAfter stirring at ambient temperature for 3 h
  4. customthe volatile organic solvents were removed under reduced pressure
  5. customthe crude product was purified by flash column chromatography (120 g of silica gel, eluting with 0-15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-bf3dc55b43e7447fa655cef86f6b0b9a
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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