Sodium Hydroxide → Bis(3-hydroxypropyl)-t-butylcarboxamide

HRID 1707839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707839
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][OH:9].[OH-].[Na+].N(C(O[C:18]([CH3:21])([CH3:20])[CH3:19])=O)=[N+]=[N-].C([O-])(=O)C[C:24](CC([O-])=O)(C([O-])=O)[OH:25].[Na+].[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O.CCOCC>[OH:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][OH:9])[C:24]([C:18]([CH3:19])([CH3:20])[CH3:21])=[O:25]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 106986DipropanolamineHCID 21863217Citric acid sodium citrate

Produkt 1

HCID 18962084Bis(3-hydroxypropyl)-t-butylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

Dissolve bis(3-hydroxypropyl)amine (1.33 g, 10 mmol) in 50/50 dioxane/water (25 mL) and buffer to pH 10 with 1N sodium hydroxide. Add, by dropwise addition, an ether solution of t-butyl azidoformate (1.58 g, 11 mmol) at 10° C. Allow to warm to room temperature and buffer occasionally to retain pH 10. Acidify with a sodium citrate/citric acid buffer to pH 5, extract with ether (3X), dry (MgSO4) and evaporate the solvent in vacuo. Purify the residue by silica gel chromatography to give bis(3-hydroxypropyl)-t-butylcarboxamide. Dissolve 3,5-di-t-butyl-4-hydroxy-N-[(4-methylphenyl)sulfonyl]-aniline (142 mg, 0.43 mmol) in anhydrous tetrahydrofuran (3 mL) and add triphenylphosphine (168 mg, 0.645 mmol). Stir under a nitrogen atmosphere and add bis(3-hydroxypropyl)-t-butylcarboxamide (83.6 mg, 0.215 mmol) followed by diethyl azodicarboxylate (0.083 mL, 0.530 mmol). Stir at room temperature for several hours and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound.

Aufarbeitung

  1. additionAdd, by dropwise addition
  2. customat 10° C
  3. extractionextract with ether (3X)
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify the residue by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5440587a7c074f3eadb0616af3c36cbb
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05354782

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