Hydrochloric Acid → HCID 86639986, compound

HRID 1359922Notes

Reaction equation

[CH2:1]([C:3]1[CH:43]=[CH:42][C:6]([CH2:7][C:8]2[C:13]([C:14]#[N:15])=[C:12]([O:16]C)[CH:11]=[C:10]([C@:18]3([O:36][C@H:35]([CH2:37][O:38]C(=O)C)[C@@H:30]([O:31]C(=O)C)[C@H:25]([O:26]C(=O)C)[C@H:20]3[O:21]C(=O)C)[OH:19])[CH:9]=2)=[CH:5][CH:4]=1)[CH3:2].Cl.[NH+]1C=CC=CC=1.[OH-].[Na+].Cl>CO>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[C:13]([C:14]#[N:15])=[C:12]([OH:16])[CH:11]=[C:10]([C@:18]3([O:36][C@H:35]([CH2:37][OH:38])[C@@H:30]([OH:31])[C@H:25]([OH:26])[C@H:20]3[OH:21])[OH:19])[CH:9]=2)=[CH:42][CH:43]=1)[CH3:2]

Participants

Conditions

Temperature: 215 °C

Procedure

A mixture of 6-(4-ethylbenzyl)-2-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzonitrile (0.36 g) and pyridinium hydrochloride (0.72 g) is heated at 215° C. for 1.5 h. After cooling to ambient temperature, the mixture is dissolved in methanol (8 mL) and treated with 4 M aqueous NaOH solution (2.5 mL). The solution is stirred at room temperature for 1 h and then acidified using hydrochloric acid (4 mol/L). After removal of the organic solvents, the residue is extracted with ethyl acetate, the combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water).

Workup

temperatureAfter cooling to ambient temperature
customAfter removal of the organic solvents
extractionthe residue is extracted with ethyl acetate
dry with materialthe combined organic extracts are dried (sodium sulphate)
customthe solvent is evaporated
customThe remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water)

Sources & evidence

ORD record: ord-aa4e83a6c087488784e05cfdc9a5523c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879806B2

Reaction notes

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