Sodium Azide → HCID 86639452, compound

HRID 451831Notes

Reaction equation

HRID 451831 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][C@@H:17]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:18][C@H:19]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:20]2)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[N:1]([CH2:16][C@@H:17]([NH:26][C:27](=[O:28])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:18][C@@H:19]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:20]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59201342HCID 59201342, compound

Product 1

HCID 86639452HCID 86639452, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of NaN3 (47 mg, 0.72 mmol) and (S)-2-(tert-butoxycarbonylamino)-3-((R)-oxepan-3-yl)propyl 4-methylbenzenesulfonate (103 mmol, 0.24 mmol) in anhydrous DMF was heated to 80° C. for 2 h. After cooling to rt, the reaction was diluted with EtOAc and washed with H2O, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel to give tert-butyl (S)-1-azido-3-((S)-oxepan-3-yl)propan-2-ylcarbamate. MS ESI +ve m/z 321 (M+Na).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e1c9c572d6ab47da9cf07f678ceae67f
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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