HCID 20505601, compound → HCID 20505517, compound

HRID 355269Notes

Reaction equation

HRID 355269 reaction equation
[N:1]([CH:4]([CH2:13][CH3:14])[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7])=[N+:2]=[N-:3]>FC(F)(F)C(O)=O>[N:1]([CH:4]([CH2:13][CH3:14])[CH2:5][C:6]([OH:8])=[O:7])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 20505601HCID 20505601, compound

Product 1

HCID 20505517HCID 20505517, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

t-Butyl 3-azidopentanoate (1.84 g, 9.23 mmol) was dissolved in 99% trifluroacetic acid (2 ml) and stirred at room temperature for 1 h and evaporated to dryness. The traces of solvent and isobutylene were removed in vacuo to give an oily substance (990 mg, 44.0%). ir (neat) νmax : 3100 (broad, OH), 2100 (N3) and 1710 cm-1 (C=O of acid); 1Hmr (CDCl3) δ: 1.06 (3H, t), 1.60 (2H, q), 2.57 (2H, d), 3.43 (H, m) and 11.73 ppm (H, s). Anal. calcd for C5H9N3O2 : C 41.95, H 6.33; found: C 41.22, H 6.05.

Workup

  1. customevaporated to dryness
  2. customThe traces of solvent and isobutylene were removed in vacuo
  3. customto give an oily substance (990 mg, 44.0%)

Sources & evidence

ORD record
ord-e48b0053744941a1b10b6b0025798fef
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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