Triethylamine → HCID 117702214, compound

HRID 1525296Notes

Reaction equation

HRID 1525296 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.BrC1C=CC(C(CC(C)([S@@](N)=O)C)C2CCCCC2)=CC=1.[CH3:43][PH:44]([O-])([O-:48])[O:45][CH2:46][CH3:47].CCN(CC)CC>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:16]1([C@H:8]([NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[C:5]2[CH:6]=[CH:7][C:2]([P:44]([CH3:43])(=[O:48])[O:45][CH2:46][CH3:47])=[CH:3][CH:4]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 89462303HCID 89462303, compoundHCID 131733144HCID 131733144, compoundHCID 178476778HCID 178476778, compound

Product 1

HCID 117702214HCID 117702214, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To (S)—N—((S)-(4-bromophenyl)(cyclohexyl)methyl)-2-methylpropane-2-sulfinamide, 27-b. (4.887 g, 13.13 mmol), ethyl methylphosphite (2.84 g, 26.26 mmol) and Et3N (3.98 g, 39.4 mmol) in THF (100 ml) was added PdCl2(dppf) (1.5 g). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken into dichloromethane and washed with brine. The organic layer was concentrated under vacuum and the residue was purified over silica gel (diluting with ethyl acetate) to provide the product, 27-c, (5.0 g, 90%).

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe residue was purified over silica gel (diluting with ethyl acetate)

Sources & evidence

ORD record
ord-f77f256bd2054e8c89f01eb4716a48c1
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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