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

HRID 571228ノート

反応式

HRID 571228 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-e8986861874d47a08d71dfed2de800fe
出典データセット
uspto-grants-2015_05
特許番号
US09024027B2

反応ノート

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