Benzhydrylamine → methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate

HRID 8835

Reaktionsgleichung

Reaktionsgleichung von HRID 8835
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[S:23]([CH2:26][C@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])(=[O:25])=[O:24]>C(Cl)Cl>[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][S:23]([CH2:26][C@H:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])(=[O:25])=[O:24])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 18738451methyl 3-chlorosulfonyl-2(R)-methylpropionate

Produkt 1

HCID 18738453methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionateAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1 g aminodiphenylmethane, 2 mL triethylamine in 20 mL CH2Cl2. The reaction was cooled to 0° C. and 1 g of methyl 3-chlorosulfonyl-2(R)-methylpropionate was slowly added. The reaction was stirred 1 hour then concentrated in vacuo. The residue was partioned between ethyl acetate and water. The organic phase was washed with brine, dried, and concentrated in vacuo. Trituration from Et2O/hexanes gave 1.15 g of methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate as a white solid. HRMS (M+Li): calcd. 354.1351, obs 354.1569.

Aufarbeitung

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. concentrationthen concentrated in vacuo
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-defc4ba15708436b96ff3719a741c0e0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091219B2

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