1H-Benzotriazole-1-carboxaldehyde → HCID 86585982, compound

HRID 1935628Notes

Reaction equation

HRID 1935628 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])[CH:16]=2)[NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:30](N1C2C=CC=CC=2N=N1)=[O:31]>C1COCC1>[Si:1]([O:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])[CH:16]=2)[N:11]1[CH:30]=[O:31])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 69949710HCID 69949710, compound

Product 1

HCID 86585982HCID 86585982, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of the product from Step 9 (0.39 g, 0.93 mmol) and THF (15 ml), under nitrogen is treated with N-formylbenzotriazole (0.164 g, 1.12 mmol) and kept at ambient temperature for 1 h. It is then concentrated in vacuo. Chromatography of the residue on silica gel with mixtures of acetone-methylene chloride containing 20-40% acetone gave 0.37 g of the titled product: 1H NMR (300 MHz, CDCl3) δ0.00 (m, 6H), 0.73, 0.86 (s, s, 9H), 2.02 (s, 3H), 2.70, 3.23 (m, m, 2H), 3.68 (m, 5H), 4.03 (m, 1H), 4.43, 4.80 (m, m, 1H), 4.75 (m, 1H), 6.14 (m, 1H), 7.08, 7.20, 7.47, 7.61, 8.04 (m, 3H), 8.52, 8.86 (s, s, 1H).

Workup

  1. concentrationIt is then concentrated in vacuo

Sources & evidence

ORD record
ord-d862bdba76294e9ba1208c0b8555d8ae
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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