2-Methyl-2-butene → 2-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

HRID 588500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588500
[CH:1]([C:3]1[S:7][C:6]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N:5][CH:4]=1)=[O:2].O.O.P([O-])(O)(O)=[O:21].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:13]([O:12][C:11]([NH:10][CH:8]([C:6]1[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][N:5]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

Komponenten

7

Edukt 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86657335Tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate

Produkt 1

HCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acidAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate (3.5 g, 0.014 mol), sodium dihydrogen phosphate dihydrate (2.9 g, 0.019 mol) and 2-methyl-2-butene (3.85 g, 0.055 mol) in tert-butyl alcohol (70 ml) and water (40 mL) was stirred at room temperature for 30 minutes. Sodium chlorite (3.22 g, 0.035 mol) was added and the reaction maintained at room temperature for an additional 2 hours. The reaction was concentrated, diluted with water (50 mL) and acidified (pH=4) with the addition of 3N H3PO4. The mixture was extracted with DCM, the organic layer dried over anhydrous Na2SO4 and evaporated to dryness to afford 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (2.35 g, 60%). LC-MS: (FA) ES+ 273.

Aufarbeitung

  1. temperaturethe reaction maintained at room temperature for an additional 2 hours
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water (50 mL)
  4. additionwith the addition of 3N H3PO4
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe organic layer dried over anhydrous Na2SO4
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-70f31c8f91b149c1b20024a757314c11
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227951B2

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