Triethylamine → methanesulfonic acid 2-(2-isopropyl-2H-tetrazol-5-yl)-ethyl ester

HRID 1802789Notes

Reaction equation

HRID 1802789 reaction equation
[CH:1]([N:4]1[N:8]=[N:7][C:6]([CH2:9][CH2:10][OH:11])=[N:5]1)([CH3:3])[CH3:2].[CH:12]([N:15]1[C:19]([CH2:20][CH2:21][OH:22])=[N:18][N:17]=[N:16]1)([CH3:14])[CH3:13].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[CH:1]([N:4]1[N:8]=[N:7][C:6]([CH2:9][CH2:10][O:11][S:24]([CH3:23])(=[O:26])=[O:25])=[N:5]1)([CH3:3])[CH3:2].[CH:12]([N:15]1[C:19]([CH2:20][CH2:21][O:22][S:24]([CH3:23])(=[O:26])=[O:25])=[N:18][N:17]=[N:16]1)([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578992162-(2-isopropyl-2H-tetrazol-5-yl)-ethanolHCID 578992222-(1-isopropyl-1H-tetrazol-5-yl)-ethanol

Product 2

HCID 57899250methanesulfonic acid 2-(1-isopropyl-1H-tetrazol-5-yl)-ethyl esterYield 4%HCID 57899307methanesulfonic acid 2-(2-isopropyl-2H-tetrazol-5-yl)-ethyl esterYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2(2-isopropyl-2H-tetrazol-5-yl)-ethanol and 2-(1-isopropyl-1H-tetrazol-5-yl)-ethanol (1.5 g, 9.6 mmol) in methylene chloride (40 mL) was added methanesulfonyl chloride (0.82 mL, 11 mmol) and triethylamine (2.67 mL, 19.2 mmol). The solution was stirred at room temperature for 6 h, loaded on to a silica gel column, and eluted using methylene chloride/heptane followed by ethyl acetate/methylene chloride to provide methanesulfonic acid 2(2-isopropyl-2H-tetrazol-5-yl)-ethyl ester (370 mg, 17% yield) and methanesulfonic acid 2(1-isopropyl-1H-tetrazol-5-yl)-ethyl ester (80 mg, 4% yield).

Workup

  1. washeluted

Sources & evidence

ORD record
ord-8051bc2dcdde45b295a898fe66d72e87
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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