Sodium Azide → HCID 178523858, compound

HRID 539509Notes

Reaction equation

HRID 539509 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10](C#N)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:24]=[N+:25]=[N-:26].[Na+].O.C([OH:32])(C)C>[Br-].[Zn+2].[Br-]>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10]([OH:11])=[O:32])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[NH:1]1[CH:14]=[N:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 21889133Propan-2-ol--water (1/1)HCID 131731969Cbz-Phe-CN

Product 1

HCID 178523858HCID 178523858, compound

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

Cbz-Phe-CN (2.54 g, 9.06 mmole) with sodium azide (1.18 g, 18.12 mmole) and zinc bromide (1.02 g, 4.53 mmole) in a 2:1 mixture of water/isopropanol (90 ml) was then refluxed for 16 hr. The mixture was removed from heat and allowed to cool to room temperature. 1M HCL (14 ml) was added to the mixture, causing the formation of a white precipitate. Ethyl Acetate (30 ml) was then added and the mixture was stirred until the precipitate disappeared. The aqueous phase was separated and washed with ethyl acetate (70 ml). The combined organic layers were then washed with 100 ml of water containing 150 μL of 1 mM DTPA in PBS. The organic layer were dried over magnesium sulfate, filtered, and concentrated in vacuo to give Cbz-Phe-tetrazole as a white solid. (2.96 g, 91%) HPLC analysis: 99% at 6.6 min; ESMS m/z 324.24 (MH)+, 346.25 (M+Na)+

Workup

  1. temperaturewas then refluxed for 16 hr
  2. customThe mixture was removed
  3. temperaturefrom heat
  4. addition1M HCL (14 ml) was added to the mixture
  5. additionEthyl Acetate (30 ml) was then added
  6. customThe aqueous phase was separated
  7. washwashed with ethyl acetate (70 ml)
  8. washThe combined organic layers were then washed with 100 ml of water containing 150 μL of 1 mM DTPA in PBS
  9. dry with materialThe organic layer were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-754c022c8ebc4297af063f663e2ba7a5
Source dataset
uspto-grants-2014_10
Patent number
US08871720B2

Reaction notes

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