Ethanol → HCID 178467060, compound

HRID 2089040Notes

Reaction equation

HRID 2089040 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[N:25]([S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:24]=2)[CH:3]=1.N(C(OC(C)(C)C)=O)=NC(O[C:47](C)(C)[CH3:48])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:47][CH3:48])[CH:30]=3)[N:25]([S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:24]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 178453994HCID 178453994, compound

Product 1

HCID 178467060HCID 178467060, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 224a (80.0 mg, 0.134 mmol), di-tert-butyl azodicarboxylate (77 mg, 0.334 mmol), triphenylphosphine on solid support (3 mmol/g, 112.0 mg, 0.427 mmol) and ethanol (0.039 mL, 0.669 mmol) in THF (3 mL) was stirred at room temperature overnight. The mixture was diluted with EtOac, filtered through celite, concentrated and purified on a 12 g column using the ISCO Companion flash system eluting with hexane/EtOAc (8:2 to 6:4) to give 76.1 mg of the title compound.

Workup

  1. additionThe mixture was diluted with EtOac
  2. filtrationfiltered through celite,
  3. concentrationconcentrated
  4. custompurified on a 12 g column
  5. washeluting with hexane/EtOAc (8:2 to 6:4)

Sources & evidence

ORD record
ord-0296e144f2844c50a7962bfe5333d268
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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