Cyanogen Bromide → HCID 25016537, compound

HRID 600834Notes

Reaction equation

HRID 600834 reaction equation
[NH2:1][C@H:2]([CH2:5][N:6]([CH2:13][CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[N:21]#[C:22]Br>C1COCC1.CCOC(C)=O>[CH2:13]([N:6]([CH2:5][C@@H:2]1[CH2:3][O:4][C:22]([NH2:21])=[N:1]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:14]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 57667107HCID 57667107, compound

Product 1

HCID 25016537HCID 25016537, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (R)-2-amino-3-(ethyl-phenyl-amino)-propan-1-ol (235 mg) at r.t. in THF (10 ml) under an argon atmosphere were added potassium carbonate (334 mg) and a solution of cyanogen bromide (256 mg) in THF (5 ml). Stirring at r.t. was continued for 18 h. The mixture (off-white suspension) was diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient:CH2Cl2->CH2Cl2/MeOH 9:1) to provide (R)-4-[(ethyl-phenyl-amino)-methyl]-4,5-dihydro-oxazol-2-ylamine (142 mg, 54%) as off-white solid. MS (ISP): 220.1 ([M+H]+)

Workup

  1. washwashed with H2O
  2. extractionThe aqueous phase was back extracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient:CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-209937a4923045d6b85ada79863e31f9
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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