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Ethyl chloroformate → 2-(t-Butoxycarbonylaminoacetamido)-6-methylbenzyl alcohol

HRID 1762197
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1762197
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[NH2:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22][OH:23].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22][OH:23])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 15339417(2-Amino-6-methylphenyl)methanol

Produkt 1

HCID 143684552-(t-Butoxycarbonylaminoacetamido)-6-methylbenzyl alcoholAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of t-butoxycarbonylaminoacetic acid (3.5 g) in methylene chloride (50 ml) was added triethylamine (2.0 g) and then ethyl chloroformate (1.9 ml) with ice-cooling. After being stirred for 1 hour, 2-amino-6-methylbenzyl alcohol (2.74 g) was added thereto and the mixture was stirred for 7 days at an ambient temperature. To the mixture was added a saturated aqueous solution of sodium hydrogen carbonate and the organic layer was separated, washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was triturated with diethyl ether to give 2-(t-butoxycarbonylaminoacetamido)-6-methylbenzyl alcohol (1.04 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 7 days at an ambient temperature
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4fd790f3f8f046329c6a27b83f363321
Quelldatensatz
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04831041

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