Cyanogen Bromide → HCID 45100915, compound

HRID 2276371Notes

Reaction equation

HRID 2276371 reaction equation
[NH2:1][C@@H:2]([CH2:5][C@@H:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1)[CH2:7][CH3:8])[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:29]#[C:30]Br>CO.[OH-].[Na+]>[CH2:17]([O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][C@@H:6]([CH2:7][CH3:8])[CH2:5][C@H:2]1[CH2:3][O:4][C:30]([NH2:29])=[N:1]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 66705887HCID 66705887, compound

Product 1

HCID 45100915HCID 45100915, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred mixture of (2S,4S)-2-amino-4-(3-benzyloxy-phenoxy)-hexan-1-ol (90 mg) and sodium acetate (46 mg) in methanol (2 ml) under an argon atmosphere was added a solution of cyanogen bromide (37 mg) in methanol (1 ml). The mixture was stirred for 18 hours then diluted with 1 N aqueous sodium hydroxide solution. The mixture was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; gradient: dichloromethane/MeOH 100:0→95:5) to afford (S)-4-[(S)-2-(3-benzyloxy-phenoxy)-butyl]-4,5-dihydro-oxazol-2-ylamine (69 mg, 71%) as a light yellow gum. MS (ISP): 341.1 ([M+H]+).

Workup

  1. extractionThe mixture was extracted twice with dichloromethane
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; gradient: dichloromethane/MeOH 100:0→95:5)

Sources & evidence

ORD record
ord-e60ff24fef2b47d886f086f0d4016515
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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