Methanesulfonyl chloride → Methyl 2-(5,5-dimethyl-5'-(methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

HRID 571228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571228
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:6](=[O:16])[C:5]12[O:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][O:17]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:22][C:19]1([CH3:23])[CH2:20][O:21][C:5]2([C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[CH:3]=3)[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:6]2=[O:16])[O:17][CH2:18]1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 86681648Methyl 2-(5'-amino-5,5-dimethyl-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

Produkt 1

HCID 86681649Methyl 2-(5,5-dimethyl-5'-(methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(5′-amino-5,5-dimethyl-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (307 mg, 0.958 mmol) in pyridine (15 ml) was cooled to 0° C. and methanesulfonyl chloride (0.090 ml, 1.150 mmol) was added; the reaction was warmed to room temperature and stirred for 25 minutes. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N HCl; the organic phase was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography on silica gel (DCM:MeOH from 99.5:0.5 to 98.75:1.25) affording methyl 2-(5,5-dimethyl-5′-(methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (351 mg, 0.881 mmol, 92% yield). MS/ESI+ 398.9 [MH]+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1N HCl
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography on silica gel (DCM:MeOH from 99.5:0.5 to 98.75:1.25)

Quellen und Nachweise

ORD-Eintrag
ord-e8986861874d47a08d71dfed2de800fe
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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