Sodium Azide → HCID 11004210, compound

HRID 1050290Notes

Reaction equation

HRID 1050290 reaction equation
S(O[C@H:12]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[N-:39]=[N+:40]=[N-:41].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[N:39]([C@@H:12]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13]1)=[N+:40]=[N-:41]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2614443381-52-0

Product 1

HCID 11004210HCID 11004210, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

4 g (7.37 mmol) 3β-tosyloxy-5α-cholestane and 0.99 g (15.23 mmol) NaN3 are heated under stirring in 25 ml hexamethylphosphoric acid triamide (HMPT) for 3 h to 90° C. The reaction mixture is cooled and given into 100 ml ice water, the precipitated raw product subsequently removed by filtration, washed with water and dissolved in 60 ml ether. The organic phase is washed twice with water, dried over Na2SO4 and concentrated. The resulting wax-like product is directly processed further:

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe precipitated raw product
  3. customsubsequently removed by filtration
  4. washwashed with water
  5. dissolutiondissolved in 60 ml ether
  6. washThe organic phase is washed twice with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1254d54e98344097a71673dda5a47eab
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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