1-Butanesulfonyl chloride → HCID 25234239, compound

HRID 1665042Notes

Reaction equation

HRID 1665042 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)=[CH:10][CH:11]=1)[CH:2]([CH3:4])[CH3:3].C/C(/C)=C(/OC)\O[Si](C)(C)C.[CH2:33]([S:37](Cl)(=[O:39])=[O:38])[CH2:34][CH2:35][CH3:36]>ClCCl>[CH2:1]([N:5]([CH2:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)=[CH:10][CH:11]=1)[S:37]([CH2:33][CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 754301-Butanesulfonyl chlorideHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 67441398Isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amine

Product 1

HCID 25234239HCID 25234239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amine (example 15, step 2, 56 mg) in dichloromethane (1 mL) were added dimethylketene methyltrimethylsilylacetal (60 mg) and 1-butanesulfonyl chloride (41 mg). The mixture was stirred for 2 days at r.t. The mixture was diluted with dichloromethane and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1 to 1:1) to give butane-1-sulfonic acid isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amide as a colorless solid. MS: 461.4 ([M+NH4]+)

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1 to 1:1)

Sources & evidence

ORD record
ord-e8ccc94bea5341608f4f6e7bef8711fb
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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