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

HRID 1525282
Notes
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Reaction equation

HRID 1525282 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.[CH3:22][PH:23]([O-])([O-:27])[O:24][CH2:25][CH3:26].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:23]([CH3:22])(=[O:27])[O:24][CH2:25][CH3:26])[CH:7]=[CH:6][CH:5]=1)=[O:11])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89462594(R)-N-((R)-(3-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide2×HCID 178476778HCID 178476778, compound

Product 1

HCID 117702161Ethyl 3-((R)-((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

To (R)—N—((R)-(3-bromophenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide, 24-c, (11.8 g, 32.3 mmol), ethyl methylphosphite (6.5 g, 64.6 mmol) and Et3N (9.09 g, 96.9 mmol) in THF (100 ml) was added PdCl2(dppf) (2.1 g, 3.23 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, 24-d, (15 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-35a4197b6ef447a092d9058b1df67db9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079930B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes