Sodium Carbonate → 2-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine

HRID 1480173Notes

Reaction equation

HRID 1480173 reaction equation
C(OC(=O)[NH:10][C:11]([CH3:23])([C:17]1[N:21]=[C:20]([CH3:22])[O:19][N:18]=1)[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])C1C=CC=CC=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:16][S:13]([CH2:12][C:11]([NH2:10])([CH3:23])[C:17]1[N:21]=[C:20]([CH3:22])[O:19][N:18]=1)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 90203952[2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of [2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester (Example 109c, 0.085 g, 241 μmol) in dry CH2Cl2 (1 ml) under argon atmosphere cooled down at 0° C. was slowly added a 1.0M solution of boron tribromide in dichloromethane (265 μl, 265 μmol). The reaction mixture was stirred at 0° C. for 20 minutes and stirred for 1 hour at room temperature The reaction was diluted with dichloromethane and an 2.0M aqueous solution of sodium carbonate was added. The two phases mixture was stirred at room temperature for 30 minutes and was poured into a separatory funnel and the organic phase was collected. The aqueous phase was back-extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (21 mg, 40%) as yellow oil. MS (ESI, m/z): 220.3 (M+H+).

Workup

  1. stirringstirred for 1 hour at room temperature The reaction
  2. stirringThe two phases mixture was stirred at room temperature for 30 minutes
  3. additionwas poured into a separatory funnel
  4. customthe organic phase was collected
  5. extractionThe aqueous phase was back-extracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-c8641eef61ce45e3ba0cad590bbb0f66
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…