Triethylamine → Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

HRID 852624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852624
[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][CH2:2][C:3]([NH:6][C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:13])([CH3:4])[CH3:5])(=[O:24])=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Produkt 1

HCID 11659022Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl esterAusbeute 108,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl (2-hydroxy-1,1-dimethylethyl)carbamate (5.1 g, 27 mmol, 1 equiv) in CH2Cl2 (100 ml) at room temperature were added NEt3 (11.3 ml, 81 mmol, 3 equiv) and methanesulfonyl chloride (28.3 mmol, 2.2 ml, 1.05 equiv) and the resulting solution was stirred for 2 h then partitioned between AcOEt and a saturated aqueous NaHCO3 solution. The two layers were separated and the organic phase dried over MgSO4 and concentrated in vacuo to give 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-methylpropyl methanesulfonate (D273) (7.8 g, 108%) as a yellow oil which was used in the next step without further purification.

Aufarbeitung

  1. customthen partitioned between AcOEt
  2. customThe two layers were separated
  3. dry with materialthe organic phase dried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae3e04e921db464293be9b993b391562
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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