Tetrahydrofuran → HCID 178462213, compound

HRID 1094632Notes

Reaction equation

HRID 1094632 reaction equation
C1COCC1.[NH:6]1[C:10]2[CH:11]=[C:12]([C:15](=O)[CH3:16])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[CH3:18][C:19]([S@:22]([NH-:24])=[O:23])([CH3:21])[CH3:20].[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.CCO.O>[NH:6]1[C:10]2[CH:11]=[C:12]([C@H:15]([NH:24][S:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23])[CH3:16])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86609349(R)-t-butylsulfinylamideHCID 178466050HCID 178466050, compound

Product 1

HCID 178462213HCID 178462213, compound

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a THF (25 ml) solution of 1-(1H-1,2,3-benzotriazol-6-yl)ethanone (1.85 g, 11.5 mmol), (R)-(+)-2-methyl-2-propanesulfinylamide (2.30 g, 18.9 mmol) and titanium(IV) ethoxide (25 ml) were added and the mixture was stirred for 24 hours at 70° C. Then, the mixture was cooled to 0° C. and sodium borohydride (1.5 mg, 40 mmol) was added. After stirring for 2 hours, water and EtOH were added to the mixture with stirring for 1 hour at room temperature. Filtration, evaporation gave N-[(1R)-1-(1H-1,2,3-benzotriazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (99% d.e.) (MS (ESI) m/z 265 (M−H)−, 267 (M+H)+) which was treated with hydrochloric acid-MeOH (2.0 M, 15.0 ml) and 1,4-dioxane (15.0 ml) for 1.5 hours at room temperature. Then, the reaction mixture was evaporated and diethyl ether was added to form a precipitate, which was collected, washed with diethyl ether to give 1.26 g (68%) of the title compound. MS (ESI) m/z 161 (M−H)−

Workup

  1. temperatureThen, the mixture was cooled to 0° C.
  2. stirringAfter stirring for 2 hours
  3. stirringwith stirring for 1 hour at room temperature
  4. filtrationFiltration, evaporation

Sources & evidence

ORD record
ord-45e0aa29cafa4fd8aa369240598d1bfe
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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