Triphenylphosphine → HCID 68423251, compound

HRID 1443432Notes

Reaction equation

HRID 1443432 reaction equation
C([O:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@H:17]1[CH:19]=[CH2:20])=[O:7])(C)(C)C.[CH:27]1[CH:32]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:28]=1.[N:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[N:48][CH:47]=1.[S:56]1[CH:60]=[CH:59][N:58]=[CH:57]1.C[CH:62]([O:64]C(/N=N/C(OC(C)C)=O)=O)C.C([SiH](CC)CC)C>C1COCC1.C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:24]([O:23][C:21]([C:16]1([NH:15][C:14]([CH:9]2[CH2:10][CH:11]([O:13][C:49]3[C:50]4[C:55](=[CH:54][C:53]([O:64][CH3:62])=[CH:52][CH:51]=4)[N:46]=[C:47]([C:57]4[S:56][CH:60]=[C:59]([CH:27]([CH3:32])[CH3:28])[N:58]=4)[N:48]=3)[CH2:12][CH:8]2[C:6]([OH:5])=[O:7])=[O:26])[CH2:18][CH:17]1[CH:19]=[CH2:20])=[O:22])[CH3:25]

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 12052TriethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl esterHCID 68410388HCID 68410388, compound

Product 1

HCID 68423251HCID 68423251, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 15 (850.0 mg, 2.30 mmol), PPh3 (1.60 g, 6 mmol), and the thiazole quinazoline 7 (820 mg, 2.72 mmol) were dissolved in THF (30 mL) in an ice bath. DIAD (1.18 ml, 6 mmol) was added dropwise. After stirring for 30 min, the mixture was stirred at RT for 2 days and then concentrated under vacuum. Flash column chromatography (silica, EtOAc—hexane) gave the Mitsunobu product. To a solution of this product (1.04 g, 1.60 mmol) and triethylsilane (460 mg, 4.00 mmol) in DCM (30 mL), TFA (30 mL) was added dropwise at RT. The mixture was stirred for 2 h at room temperature, evaporated under reduced pressure, and coevaporated twice with toluene. Flash column chromatography (silica, 94/6 DCM-MeOH) gave the title compound as a white solid (950 mg, 70%).

Workup

  1. stirringthe mixture was stirred at RT for 2 days
  2. concentrationconcentrated under vacuum
  3. customFlash column chromatography (silica, EtOAc—hexane) gave the Mitsunobu product
  4. stirringThe mixture was stirred for 2 h at room temperature
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9fa6763acea1426ca3fc106ecc4aedc9
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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