Methanesulfonyl chloride → 1-(2-(3-carboethoxypropyloxy)-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine

HRID 323369Notes

Reaction equation

HRID 323369 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][N:34]=[N:33]2)=[CH:28][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH2:19][CH2:20][OH:21])[CH2:15]1)=[O:13])([O:3][CH2:4][CH3:5])=[O:2].C(N(CC)C(C)C)(C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl>[C:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][N:34]=[N:33]2)=[CH:28][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH2:19][CH2:20][O:21][S:47]([CH3:46])(=[O:49])=[O:48])[CH2:15]1)=[O:13])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 184650041-(2-(3-carboethoxypropyloxy)-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Product 1

HCID 184650481-(2-(3-carboethoxypropyloxy)-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 1-(2-(3-carboethoxypropyloxy)-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (0.15 g, 0.3 mmol) and dichloromethane (5 mL). Cool in an ice bath. Add N,N,-diisopropylethylamine (0.12 mL, 86.5 mg, 0.67 mmol), and methanesulfonyl chloride (0.035 mL, 52 mg, 0.46 mmol). After 2 hours, dilute the reaction mixture with dichloromethane and extract with aqueous 1 M hydrochloric acid solution, water, and then a saturated aqueous solution of sodium bicarbonate. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound: Rf=0.23 (silica gel, ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. extractionextract with aqueous 1 M hydrochloric acid solution, water
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-41b5aad401a344d0840fe3bad0cba764
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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