Ammonium Chloride → (R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

HRID 246119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246119
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].[Cl-].[NH4+]>ClCCl>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH3:11])[CH2:9][O:10][S:23]([CH3:22])(=[O:25])=[O:24])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Produkt 1

HCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonateAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

((R)-2-Hydroxy-1-methyl-ethyl)-carbamic acid tert-butyl ester (0.5 g, 2.85 mmol) was dissolved in dichloromethane (14 ml) and stirred in an ice bath. N,N-diisopropylethylamine (0.75 ml, 4.28 mmol) and then methanesulfonyl chloride (0.27 ml, 3.4 mmol) were slowly added and the reaction was warmed to room temperature over 16 h. Ammonium chloride solution was added to the reaction and it was extracted two times with ethyl acetate. The combined organics were washed with sodium chloride solution and dried over sodium sulfate. Evaporation gave 0.73 g of methanesulfonic acid (R)-2-tert-butoxycarbonylamino-propyl ester as a waxy white solid. 1H NMR (CDCl3) δ: 4.51-4.68 (m, 1H), 4.19-4.28 (m, 1H), 4.11-4.18 (m, 1H), 3.90-4.04 (m, 1H), 3.03 (s, 3H), 1.24 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. extractionwas extracted two times with ethyl acetate
  2. washThe combined organics were washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-19275734b0c84c158d1a3dc796f53c11
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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