tert-Butylsulfinamide, (R)-(+)- → HCID 86649303, compound

HRID 1523238Notes

Reaction equation

HRID 1523238 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)[CH3:9])=[CH:4][CH:3]=1.[CH3:22][C:23]([S@:26]([NH2:28])=[O:27])([CH3:25])[CH3:24]>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13](=[N:28][S@@:26]([C:23]([CH3:25])([CH3:24])[CH3:22])=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 59627231HCID 59627231, compound

Product 1

HCID 86649303HCID 86649303, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of (S)-3-(1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)propan-1-one (14.5 g, 0.04 mol), (R)-2-methylpropane-2-sulfinamide (5.5 g, 0.046 mol), and Ti(OEt)4 (18 g, 0.08 mmol) in THF (150 mL) was heated to reflux overnight. The mixture was treated with brine, and the precipitate was filtered. The filtrate was concentrated to give (R)—N-(3-((1S)-1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl)propylidene)-2-methylpropane-2-sulfinamide (13.3 g, 59%), which was used for the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe precipitate was filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8d1839bdefda4e2ba78b61c2324342b0
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

Loading…