1H-Benzotriazole-1-carboxaldehyde → HCID 86594252, compound

HRID 488365Notes

Reaction equation

HRID 488365 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][NH:12][CH2:11][CH2:10]3)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[O:3]1.N1([CH:35]=[O:36])C2C=CC=CC=2N=N1>C1COCC1>[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([CH:35]=[O:36])[CH2:11][CH2:10]3)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[O:3]1

Participants

4

Reactant 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 86585911HCID 86585911, compound

Product 1

HCID 86594252HCID 86594252, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dimethylethyl [[(5S)-2-oxo-3-[1,2,3,4-tetrahydro-6-isoquinolinyl]-5-oxazolidinyl]methyl]carbamate (Step 2, 292 mg, 0.841 mmol) in dry THF (16.8 mL) is treated with 1H-benzotriazol-1-carboxaldehyde (148 mg, 1.01 mmol), and the resulting suspension is stirred at ambient temperature for 1.25 hrs and is then concentrated to remove THF. The residue is rediluted with CH2Cl2 (25 mL), washed with 1N aqueous NaOH (2×10 mL) and brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure to give the crude product which is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with MeOH/CH2Cl2 (2.5/97.5). Those fractions with an Rf=0.60 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated to give 310 mg (98%) of the title compound as an amorphous, glassy solid. MS (ESI+) for C19H25N3O5 m/z 376 (M+H)+.

Workup

  1. concentrationis then concentrated
  2. customto remove THF
  3. additionThe residue is rediluted with CH2Cl2 (25 mL)
  4. washwashed with 1N aqueous NaOH (2×10 mL) and brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product which
  8. customis then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  9. washeluting with MeOH/CH2Cl2 (2.5/97.5)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-44cddcaeb9b247b180942146060d8316
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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