Acetaldehyde → HCID 22662419, compound

HRID 2304357Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C[Li].C([Li])(C)(C)C.[CH:31](=[O:33])[CH3:32]>C(OCC)C.O>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:10]([CH:31]([OH:33])[CH3:32])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

3.3 g (0.01 mol) (4-tert.butoxycarbonylamino-3-bromophenyl)carbamic acid-tert.-butyl ester are dissolved in 200 ml diethyl ether under argon. Then first 20 ml of a 1.6 molar methyl lithium solution are added at −25° C. and then 16 ml of a 1.6 molar tert.-butyl lithium solution are added. After one hour 1.2 ml (0.02 mol) of acetaldehyde are added and the reaction mixture is slowly heated to 20° C. After halting the reaction the reaction mixture is hydrolyzed with water, the organic phase is extracted with dilute sodium hydroxide and then dried with magnesium sulfate. The solvent is distilled off in a rotary evaporator and the residue is purified with petroleum ether/acetic acid ethyl ester (8:2). 3.0 g (85% of theoretical) of (4-tert.-butoxycarbonylamino-3-(1-hydroxyethyl)phenyl)carbamic acid-tert.-butyl ester having a melting point of 189° C. are obtained.

Workup

customthe reaction the reaction mixture
extractionthe organic phase is extracted with dilute sodium hydroxide
dry with materialdried with magnesium sulfate
distillationThe solvent is distilled off in a rotary evaporator
customthe residue is purified with petroleum ether/acetic acid ethyl ester (8:2)

Sources & evidence

ORD record: ord-9711769a055247ee8c28e852f87e7298
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436152B1

Reaction notes

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