HCID 18753701, compound → HCID 18753689, compound

HRID 1838450Notes

Reaction equation

HRID 1838450 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][CH:8]([NH:10]C(OC(C)(C)C)=O)[CH:7]=[CH:6]1)=[N+:2]=[N-:3]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:1]([CH2:4][CH:5]1[CH2:9][CH:8]([NH2:10])[CH:7]=[CH:6]1)=[N+:2]=[N-:3]

Participants

4

Reactant 1

HCID 18753701HCID 18753701, compound

Product 1

HCID 18753689HCID 18753689, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-[4-(azidomethyl)cyclopent-2-enyl](t-butoxy)-carboxamide (10 g, 42 mmol) was dissolved in TFA reagent (9.25 mL TFA, 0.25 mL anisole, 0.25 mL triisopropylsilane and 0.25 mL water)and DCM (25 mL), and stirred for 30 min at rt. The reaction mixture was concentrated and the residue filtered through SCX column, eluted with ammonia (2 M solution in methanol), and evaporated to yield the title compound (4.6 g, 80%).: ESMS: 139 (M+1)+. 1H NMR (CDCl3): δ 1.40-1.55 (m, 1H), 2.45-2.60 (m, 1H), 2.90-3.00 (m, 1H), 3.40 (d, 2H), 4.104.20 (m, 1H), 5.90 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe residue filtered through SCX column
  3. washeluted with ammonia (2 M solution in methanol)
  4. customevaporated

Sources & evidence

ORD record
ord-a2d57e4a28014897bf25afe5431f19ce
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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