4-Methylmorpholine → tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate

HRID 32815

Reaktionsgleichung

Reaktionsgleichung von HRID 32815
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[CH3:36][NH:37][O:38][CH3:39].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:37]([O:38][CH3:39])[CH3:36])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

Produkt 1

HCID 58604314tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamateAusbeute 88.069,203 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (14 g, 0.0573 mol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (10.06 g, 0.0573 mol) and N-methyl morpholine (5.79 g, 0.0573 mol) in tetrahydrofuran was stirred for 2 hours at room temperature. N,O-Dimethylhydroxylamine hydrochloride (5.59 g, 0.0573 mmol) and triethylamine (5.59 g, 0.0573 mol) were added and the mixture was stirred for 3 days. The reaction mixture was evaporated and ethyl acetate was added. The reaction mixture was washed with 1 N aqueous hydrochloric acid and then washed with saturated aqueous sodium bicarbonate. [4-(Methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (14.5 g, 88%) was obtained as a tan tar after drying (magnesium sulfate) and evaporation.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with 1 N aqueous hydrochloric acid
  4. washwashed with saturated aqueous sodium bicarbonate

Quellen und Nachweise

ORD-Eintrag
ord-59be9c7ae1d246e5bf7b527b4f99c272
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427635B2

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