Water → HCID 131726334, compound

HRID 1271489Notes

Reaction equation

HRID 1271489 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][N:8]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[C:7]1=[O:30].O>CN(C)C=O>[C:16]([O:15][C:13]([N:11]1[CH2:12][C@@H:6]([N:1]=[N+:2]=[N-:3])[C:7](=[O:30])[N:8]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH2:9][C@@H:10]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 18451947HCID 18451947, compound

Product 1

HCID 131726334HCID 131726334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium azide (0.841 g, 12.9 mmol) was added to a solution of tert-butyl 6-bromo-4-(cyclopropylmethyl)-5-oxo-2-phenyl-1,4-diazepane-1-carboxylate (0.609 g, 1.43 mmol) in N,N-dimethylforamide (10 mL) and heated to 70° C. After 1 h, the mixture was allowed to cool to ambient temperature and water was added. The mixture was extracted with ethyl acetate, washed with water (3×), saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (20% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave 170 mg of the trans isomer and 30 mg of the cis isomer. MS 386 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water (3×), saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (20% ethyl acetate/hexanes→50% ethyl acetate/hexanes)
  8. customgave 170 mg of the trans isomer and 30 mg of the cis

Sources & evidence

ORD record
ord-761459ed64ff4a40819bc19119e4da85
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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