Triphenylphosphine → HCID 59737515, compound

HRID 1907736Notes

Reaction equation

HRID 1907736 reaction equation
O[C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:35]=[CH:34][C:11]([C:12]([NH:14][C:15]3[CH:20]=[C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[CH:18]=[CH:17][C:16]=3[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:13])=[CH:10][CH:9]=2)[CH2:3]1.[N+:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH:48][C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)(=[O:47])=[O:46])=[CH:41][CH:40]=1)([O-:38])=[O:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N+:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([N:48]([C@H:2]2[CH2:6][CH2:5][N:4]([CH2:7][C:8]3[CH:35]=[CH:34][C:11]([C:12]([NH:14][C:15]4[CH:20]=[C:19]([C:21]5[S:22][CH:23]=[CH:24][CH:25]=5)[CH:18]=[CH:17][C:16]=4[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:13])=[CH:10][CH:9]=3)[CH2:3]2)[C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)(=[O:46])=[O:47])=[CH:41][CH:40]=1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 771980HCID 771980, compoundHCID 59737572HCID 59737572, compound

Product 1

HCID 59737515HCID 59737515, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 243 (0.98 g, 1.81 mmol) in THF (10 mL) at 0° C., was added compound 246 (0.61 g, 2.17 mmol), triphenylphosphine (0.76 g, 2.89 mmol) and diethyl azodicarboxylate (DEAD) (0.51 g, 2.90 mmol), the ice bath was removed and the reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was partitioned between EtOAc and H2O, organic phase was collected, washed successively with saturated NH4Cl and brine, dried over MgSO4, filtered and concentrated to give a light brown oil which was purified by flash chromatography (eluent: 50% AcOEt in hexanes to 100% AcOEt) to give intermediate 247 (0.65 g, 47% yield).

Workup

  1. customthe ice bath was removed
  2. customThe reaction mixture was partitioned between EtOAc and H2O, organic phase
  3. customwas collected
  4. washwashed successively with saturated NH4Cl and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light brown oil which
  9. customwas purified by flash chromatography (eluent: 50% AcOEt in hexanes to 100% AcOEt)

Sources & evidence

ORD record
ord-b6c480300144445099fba8523b47f449
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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