Triphenylphosphine → HCID 86759668, compound

HRID 1816016Notes

Reaction equation

HRID 1816016 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]1[CH:17]=[C:18]([C@@H:22]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[CH:20][CH:21]=1.[N:37]1[C:46]2[NH:45][CH2:44][CH2:43][CH2:42][C:41]=2[CH:40]=[CH:39][C:38]=1[CH2:47][CH2:48]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:15][C:16]1[CH:17]=[C:18]([C@@H:22]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:48][CH2:47][C:38]3[CH:39]=[CH:40][C:41]4[CH2:42][CH2:43][CH2:44][NH:45][C:46]=4[N:37]=3)=[CH:34][CH:35]=2)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11367331HCID 11367331, compoundHCID 69816255HCID 69816255, compound

Product 1

HCID 86759668HCID 86759668, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.20 mL, 1.0 mmole) was added dropwise to a solution of ethyl (S)-3-(3-fluorophenyl)-4-(4-hydroxyphenyl)butanoate (250 mg, 0.83 mmole), 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-1-ethanol (178 mg, 1.0 mmole), and triphenylphosphine (262 mg, 1.0 mmole) in anhydrous THF (5 mL) at RT. After 18 hr the reaction was concentrated and the residue was flash chromatographed on silica gel (5:1 Et2O/hexanes) to afford impure title compound (236 mg, 61%): MS (ES) m/e 463 (M+H)+. This was used without further purification.

Workup

  1. concentrationAfter 18 hr the reaction was concentrated
  2. customchromatographed on silica gel (5:1 Et2O/hexanes)

Sources & evidence

ORD record
ord-8d8d9ec73d494102aa8f559f051749e3
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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