Tributyltin azide → HCID 178501433, compound

HRID 1289245Notes

Reaction equation

HRID 1289245 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][CH2:18][C:19]#[N:20])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([N:34]=[N+:35]=[N-:36])(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][CH2:18][C:19]1[NH:36][N:35]=[N:34][N:20]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 11000307Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

Product 1

HCID 178501433HCID 178501433, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate (10 g), tri-n-butyltin azide [prepared according to the method in Rec. Trav. Chim. Pavs-Bas, 1963, 81, 286; 12 g] and THF (60 ml) was stirred and heated to reflux for 40 hours. The mixture was evaporated. The resultant brown oil was triturated in diethyl ether which had been saturated with hydrogen chloride gas. The precipitate was isolated and washed with diethyl ether. There was thus obtained methyl (2S)-2-benzyloxycarbonyl-amino-4-(tetrazol-5-yl)butyrate (2.23 g, 32%);

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureto reflux for 40 hours
  4. customThe mixture was evaporated
  5. customThe resultant brown oil was triturated in diethyl ether which
  6. customThe precipitate was isolated
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-77920b139f7b4a9cab611e6548807e5f
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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