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Acetaldehyde → HCID 22662419, compound

HRID 392007
Notes
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Reaction equation

HRID 392007 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 154289672,5-Bis-tert.-butyloxycarbonylaminobromobenzeneHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22662419HCID 22662419, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent

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

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

Sources & evidence

ORD record
ord-17f46f9672c74e3799b1c3418dd0ef4e
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800097B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes