Triethylamine → HCID 19935754, compound

HRID 37714Notes

Reaction equation

[ClH:1].Cl[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[CH:16][CH:17]=3)[C:12]([CH2:31]C(O)=O)=[C:11]2[CH3:35])=[CH:5][CH:4]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.Cl.[NH2:54][OH:55].C([N:58]([CH2:61]C)CC)C>C1C=CC=CC=1.O>[Cl:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[CH:16][CH:17]=3)[C:12]([CH2:31][NH:58][C:61]([NH:54][OH:55])=[O:43])=[C:11]2[CH3:35])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the acid of Example 16 (0.72 g, 1.52 mmol), in benzene (25 mL) is added triethylamine (0.23 mL, 1.1 equiv) followed by diphenylphosphoryl azide (0.46 g, 1.1 equiv). After the reaction mixture is heated at 90° C. for 1 hour, a solution of hydroxylamine hydrochloride (0.23 g, 2.2 equiv.) in a mixture of triethylamine (0.46 mL) and water (0.25 mL) is added to it, and the reaction mixture is heated at 90° C. overnight. The reaction is quenched by addition of ammonium chloride solution, and the resulting precipitate is filtered off, washed with water and ethyl acetate and dried to afford 0.45 g (59%) of a white solid, m.p. 184°-186° C.

Workup

additionis added to it
temperaturethe reaction mixture is heated at 90° C. overnight
customThe reaction is quenched by addition of ammonium chloride solution
filtrationthe resulting precipitate is filtered off
washwashed with water and ethyl acetate
customdried

Sources & evidence

ORD record: ord-27776c957e4343d59255aca01ddb7ea4
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420289

Reaction notes

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