1-Hydroxybenzotriazole → HCID 57462011, compound

HRID 2422337Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.Cl.[C:10]([O:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH2:17])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[C:10]([O:14][C:15](=[O:19])[C@@H:16]([NH:17][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:8])[CH3:18])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1H-imidazole-2-carboxylic acid (0.17 g) in N,N-dimethylformamide (DMF) (3 mL) was added alanine tert-butyl ester hydrochloride (0.22 g), diisopropylethyl amine (0.27 mL) and HOBT (0.41 g) before cooling to 0° C. and the reaction mixture was then treated with EDC HCl (0.32 g). The cooling bath was removed and the reaction mixture was stirred at ambient temperature for 18 hrs before being diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to afford the sub-title compound as a colourless oil (0.263 g, 73%): 1H NMR 400 MHz CDCl3 1.50 (9H, s), 1.51 (3H, d, J 7.2), 3.70 (1H, m), 7.28 (2H, s), 7.78 (1H, d, J 7.6), 11.49 (1H, br s).

Workup

customThe cooling bath was removed
additionbefore being diluted with ethyl acetate
washwashed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure
customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4d23989d38f14ac18bcd854dc51e8298
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960398B2

Reaction notes

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