Methylamine → (2S)-[4-(4-Aminobutyl)benzenesulfonylamino]-3-methylbutyramide

HRID 252172Notes

Reaction equation

HRID 252172 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C@@H:26]([CH:30]([CH3:32])[CH3:31])[C:27]([NH2:29])=[O:28])(=[O:24])=[O:23])=[CH:18][CH:17]=1.CN>>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][C@@H:26]([CH:30]([CH3:32])[CH3:31])[C:27]([NH2:29])=[O:28])(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 58912945(2S)-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]benzenesulfonylamino}-3-methylbutyramide

Product 1

HCID 58649579(2S)-[4-(4-Aminobutyl)benzenesulfonylamino]-3-methylbutyramideYield 54.8%

Procedure

A mixture of (2S)-{4-[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)butyl]-benzenesulfonylamino}-3-methylbutyramide 14 (0.40 g, 0.87 mmol) and methylamine (2 M in methanol, 20 mL, 40 mmol) was stirred at room temperature overnight. Solvent was removed by rotary evaporation and the residue was purified by flash silica gel column chromatography eluting with chloroform/methanol/concentrated ammonium hydroxide (3:1:0.1, v/v) to give (2S)-[4-(4-aminobutyl)benzenesulfonylamino]-3-methyl-butyramide (15) as a white powder (156 mg, 54% yield). 1H NMR (300 MHz, CD3OD) δ 0.85 (d, 3H), 0.87 (d, 3H), 1.66 (m, 4H), 1.90 (m, 1H), 2.69 (m, 4H), 3.51 (d, 1H), 7.35 (d, 2H) 7.75 (d, 2H). m/z (ESI): 328 [C15H25N3O3S+H]+.

Workup

  1. customSolvent was removed by rotary evaporation
  2. customthe residue was purified by flash silica gel column chromatography
  3. washeluting with chloroform/methanol/concentrated ammonium hydroxide (3:1:0.1

Sources & evidence

ORD record
ord-bf26d507cf9d4ce7a8331b5ac26bf53a
Source dataset
uspto-grants-2011_01
Patent number
US07868010B2

Reaction notes

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