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

HRID 571228Notes

Reaction equation

HRID 571228 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-e8986861874d47a08d71dfed2de800fe
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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