Sodium Azide → HCID 86761676, compound

HRID 1875356Notes

Reaction equation

HRID 1875356 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([CH2:22]OS(C)(=O)=O)[CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:22][C@@H:12]1[CH2:11][C@@H:10]([NH:9][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:8])[CH2:14][N:13]1[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium Azide2×HCID 42643385HCID 42643385, compound

Product 1

HCID 86761676HCID 86761676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

330.0 mg (0.75 mmol) tert. Butyl (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-methanesulphonyloxymethyl-pyrrolidine-1-carboxylate are dissolved in 20 ml DMF and combined with 146.6 mg (2.3 mmol) sodium azide. The mixture is stirred at 50° C. for 16 hours. Then a further 73 mg (1.12 mmol) sodium azide are added and the mixture is stirred for a further two hours at 50° C. Then it is concentrated i. vac. The residue is combined with water/sat. Saline solution and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. stirringthe mixture is stirred for a further two hours at 50° C
  2. concentrationThen it is concentrated i
  3. extractionSaline solution and extracted three times with ethyl acetate
  4. customThe combined organic phases are dried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated down i

Sources & evidence

ORD record
ord-6b4b822780094e3aa788f9520514eb0b
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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