Cyanogen Bromide → HCID 56836119, compound

HRID 2276384Notes

Reaction equation

HRID 2276384 reaction equation
[NH2:1][C@H:2]([CH2:21][OH:22])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+].[N:28]#[C:29]Br.[OH-].[Na+]>CO>[NH2:28][C:29]1[O:22][CH2:21][C@H:2]([CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[N:1]=1

Participants

6

Reactant 4

HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 66705917HCID 66705917, compound

Product 1

HCID 56836119HCID 56836119, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of N-[4-((S)-3-Amino-4-hydroxy-butyl)-phenyl]-4-chloro-benzamide (250 mg) and sodium acetate (124 mg) in methanol (10 ml) was added dropwise a solution of cyanogen bromide (100 mg) in methanol (3 ml). The resulting pale yellow solution was then stirred at room temperature for 16 h. The reaction mixture was poured into 1 N aq. NaOH and extracted twice with dichloromethane/THF. The combined organic layers were washed with sat. aq. NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel; eluant: 0% to 100% EtOAc in heptane, then 0% to 30% MeOH in EtOAc) to afford N-{4-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-4-chloro-benzamide (150 mg, 56%) as a white solid. MS (ISP): 346.1 ([{37Cl}M+H]+), 344.2 ([{35Cl}M+H]+).

Workup

  1. extractionextracted twice with dichloromethane/THF
  2. washThe combined organic layers were washed with sat. aq. NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-28b0d2aa378b44c88745de2804ef9b1d
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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