1-Hydroxybenzotriazole → HCID 57677333, compound

HRID 492908Notes

Reaction equation

HRID 492908 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[CH3:6][C:7]([O:10][C:11]([NH:13][CH2:14][CH2:15][C:16](O)=[O:17])=[O:12])([CH3:9])[CH3:8].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[N:2]1([C:16](=[O:17])[CH2:15][CH2:14][NH:13][C:11](=[O:12])[O:10][C:7]([CH3:6])([CH3:8])[CH3:9])[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12308726Azetidine hydrochloride

Product 1

HCID 57677333HCID 57677333, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

After adding azetidine hydrochloride (2.96 g) to a solution of triethylamine (4.42 ml) in N,N-dimethylformamide, the mixture was stirred for 10 minutes at room temperature. Boc-beta-ALA-OH (5.00 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.59 g) and 1-hydroxybenzotriazole (5.35 g) were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine and dried over anhydrous sodium sulfate. It was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=10:1). Fractions containing the target compound were concentrated under reduced pressure to provide the title compound (5.99 g, 99.4%) as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. customThe reaction mixture was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationIt was then concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent
  7. additionFractions containing the target compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ca49354934640d08ddcc414b7de6308
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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