Potassium Carbonate → (S)-tert-butyl 4-((1,1-diethoxypropan-2-ylamino)methyl)benzo[d]thiazol-2-ylcarbamate

HRID 2274640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2274640
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].Br[CH2:12][C:13]1[C:18]2[N:19]=[C:20]([N:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:12][C:13]1[C:18]2[N:19]=[C:20]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)[CH3:6])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12398111(2S)-1,1-Diethoxy-2-propanamineHCID 670752054-Bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole

Produkt 1

HCID 86652568(S)-tert-butyl 4-((1,1-diethoxypropan-2-ylamino)methyl)benzo[d]thiazol-2-ylcarbamateAusbeute 140,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of (S)-1,1-diethoxypropan-2-amine (Compound XVIII-1) (442 mg, 3.00 mmol) in acetonitrile (5 ml) were added 4-bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole (Compound XX-1) (133 mg, 0.30 mmol) and potassium carbonate (62 mg, 0.45 mmol) and the mixture was stirred at 65° C. for 2 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (100 ml) and the mixture was washed with water (100 ml) and brine (100 ml). The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 95:5) to obtain the title compound (173 mg, yield: 71%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. washthe mixture was washed with water (100 ml) and brine (100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-f89241b128694ad89eab0846294e35b3
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126981B2

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