Water → 1-[4-Benzoyloxy-3-(benzoyloxymethyl)-1-butyl]-5-(1-azido-2-bromoethyl)uracil

HRID 732927Notes

Reaction equation

[C:1]([O:9][CH2:10][CH:11]([CH2:24][O:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:12][CH2:13][N:14]1[CH:21]=[C:20]([CH:22]=[CH2:23])[C:18](=[O:19])[NH:17][C:15]1=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+].O.[Br:39]N1C(=O)CCC1=O>COCCOC>[C:26]([O:25][CH2:24][CH:11]([CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][CH2:13][N:14]1[CH:21]=[C:20]([CH:22]([N:34]=[N+:35]=[N-:36])[CH2:23][Br:39])[C:18](=[O:19])[NH:17][C:15]1=[O:16])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 22 (510 mg, 1.14 mmol), saturated solution of sodium azide in water (300 mg, 4.6 mmol), N-bromosuccinimide (223 mg, 1.25 mmol) and 1,2-dimethoxyethane (50 ml) was stirred at 0° C. for 30 min. Removal of the solvent in vacuo gave a viscous oil which was purified by silica gel column chromatography. Elution with chloroform-methanol (96:4, v/v) yielded 23 (530 mg, 81.5%) as a syrup.

Workup

customRemoval of the solvent in vacuo
customgave a viscous oil which
customwas purified by silica gel column chromatography
washElution with chloroform-methanol (96:4, v/v)

Sources & evidence

ORD record: ord-44ab11e8afc34298a45c4f0915e4f448
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589077B2

Reaction notes

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