Water → Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-5-chloropentanoate

HRID 2084915Notes

Reaction equation

HRID 2084915 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][CH3:16])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Br[CH:28]([CH2:33][CH2:34][CH2:35][Cl:36])[C:29]([O:31][CH3:32])=[O:30].O>CN(C=O)C>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([S:3]([N:2]([CH3:1])[CH:28]([CH2:33][CH2:34][CH2:35][Cl:36])[C:29]([O:31][CH3:32])=[O:30])(=[O:5])=[O:4])=[CH:7][CH:8]=1)[C:14]#[C:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 111607834-But-2-ynyloxy-N-methyl-benzenesulfonamideHCID 15140616Methyl 2-bromo-5-chloropentanoate

Product 1

HCID 22644971Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-5-chloropentanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7.17 g (30 mmol) N-methyl-[4-(2-butynyloxy)-phenyl]sulfonamide] in 25 ml of DMF was cooled to 0° C. and 30 ml of 1M sodium hexamethyldisilazide (30 mmol) was slowly added and this mixture was stirred for 15 min and then added to a solution of 6.89 g (30 mmol) of methyl 2-bromo-5-chloropentanoate in 25 ml of DMF and was stirred at room temperature for 18 hours. The mixture was combined with water and the precipitate was collected and purified by chromatography on silica gel using hexane-ethyl acetate, 4:1 to give methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)-amino]-5-chloropentanoate Electrospray Mass Spec 410.2 (M+Na)+.

Workup

  1. stirringwas stirred at room temperature for 18 hours
  2. customthe precipitate was collected
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-e6709d2d4f9b43ffa1a40cae44343652
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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