Triethylamine hydrochloride → HCID 178524350, compound

HRID 467990Notes

Reaction equation

[C:1]([C:3]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19]2)[CH2:5][CH2:4]1)#[N:2].[N-:24]=[N+:25]=[N-:26].[Na+].Cl.C(N(CC)CC)C>[N+](C1C=CC=CC=1)([O-])=O.C(OCC)C>[NH:2]1[C:1]([C:3]2([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3([C:21]([OH:23])=[O:22])[CH2:19][CH2:20]3)[CH2:4][CH2:5]2)=[N:26][N:25]=[N:24]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of Step 3 product of Example 19 (0.38 g, 1.8 mmol) in nitrobenzene (4 mL) were added sodium azide (0.46 g, 7.1 mmol) and triethyl amine hydrochloride (0.98 g, 7.1 mmol) at room temperature. The reaction mixture was allowed to stir at 130° C. over a period of 24 h. The reaction mixture was diluted with diethyl ether (50 mL) and extracted with 2% NaOH solution (50 mL×2). The combined aqueous layer was acidified to PH=5 (1N HCl), extracted with ethyl acetate (50 mL×2), dried over sodium sulphate. The residue obtained upon evaporation of the solvent was purified through silica gel (230-400) column (50% ethyl acetate in petroleum ether) to give product as Off-white solid 120 mg (27%). mp −133.2° C.-135.0° C.

Workup

extractionextracted with 2% NaOH solution (50 mL×2)
extractionextracted with ethyl acetate (50 mL×2)
dry with materialdried over sodium sulphate
customThe residue obtained upon evaporation of the solvent
customwas purified through silica gel (230-400) column (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-8d8dbd7992d647afb87bf8cc729edac1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623897B2

Reaction notes

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