Acetic Acid → 2-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

HRID 10910Notes

Reaction equation

[N:1]([CH2:4][C:5]([NH:7][CH2:8][C:9](=[O:20])[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[O:18][CH3:19])=[O:6])=[N+:2]=[N-:3].[BH4-].[Na+].C(O)(=O)C>CO>[N:1]([CH2:4][C:5]([NH:7][CH2:8][CH:9]([OH:20])[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[O:18][CH3:19])=[O:6])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 0 °C

Procedure

In a four neck round bottomed flask 32.4 gm (0.11 mole) of 2-azido-N-(β-Oxo-2,5-dimethoxy phenehyl)-acetamide is prepared according to the step (c) and 260 ml methanol is charged and cooled to 0° C. To this 3.24 gm (0.08 mole) sodium boro hydride is added slowly over a period. After completion of the addition, the reaction mass temperature is raised to 10° C. After completion of the reaction, 10 ml of acetic acid is added. Methanol is stripped off under reduced pressure and the residue obtained is extracted with methylene dichloride. Organic layer is washed with water and methylene dichloride is distilled off. The yield was 95%.

Workup

additionis charged
additionAfter completion of the addition
temperaturethe reaction mass temperature is raised to 10° C
additionis added
customthe residue obtained
extractionis extracted with methylene dichloride
washOrganic layer is washed with water and methylene dichloride
distillationis distilled off

Sources & evidence

ORD record: ord-49b04b3396aa4f99b9f5b82ae05606ee
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094928B2

Reaction notes

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