Triethylamine → Ethyl 3-((S)-((S)-1,1dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate

HRID 1525287Notes

Reaction equation

HRID 1525287 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@H:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.BrC1C=C([C@H](CC2C=CC=CC=2)C(C)(S(N)=O)C)C=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]>[CH3:13][C:12]([CH3:15])([S@@:10]([NH:9][C@@H:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]1[CH:3]=[C:2]([P:44]([CH3:43])(=[O:48])[O:45][CH2:46][CH3:47])[CH:7]=[CH:6][CH:5]=1)=[O:11])[CH3:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 89462160HCID 89462160, compoundHCID 131733142HCID 131733142, compoundHCID 178476778HCID 178476778, compound

Product 1

HCID 117701946Ethyl 3-((S)-((S)-1,1dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate

Reagents, catalysts & solvents 2

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

Procedure

To (S)—N—((S)-(3-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide, 25-b, (17.8 g, 48.7 mmol), ethyl methylphosphite (7.9 g, 730 mmol) and Et3N (14.75 g, 146 mmol) in THF (150 ml) was added PdCl2(dppf) (3.55 g, 4.87 mmol). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum to provide the crude product, 25-c, (25 g). The crude product was used to the next step directly.

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-18d4cfe8091541f6920a7e97c2fa50c5
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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