Triethylamine → HCID 19915247, compound

HRID 1090353Notes

Reaction equation

HRID 1090353 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]([CH2:21][CH2:22][CH2:23][NH2:24])[Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>O1CCCC1>[O:13]([CH2:21][CH2:22][CH2:23][NH:24][S:9]([CH3:8])(=[O:11])=[O:10])[Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilane2×

Product 1

HCID 19915247HCID 19915247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.16 ml, 16 mmol), followed by methanesulfonyl chloride (Compound 19, 1.48 ml, 19.2 mmol) was added to a solution of 3-tert-butyldimethylsiloxy-1-propylamine (Compound 29, 2.80 g, 16 mmol) in tetrahydrofuran (60 ml) at 0° C. under argon. After stirring at room temperature overnight, the mixture was washed successively with dilute hydrochloric acid, saturated sodium bicarbonate and brine. Evaporation of the dried (magnesium sulfate) organic phase gave the title sulfonamide. 1HNMR(CDCl3): 0.04 (s, 6H), 0.87 (s, 9H), 1.76 (p, 2H, J=6.4 Hz), 2.91 (s, 3H), 3.24 (q, 2H, J=6.2 Hz), 3.74 (t, 2H, J=5.52 Hz) and 5.05 (br t, 1H).

Workup

  1. washthe mixture was washed successively with dilute hydrochloric acid, saturated sodium bicarbonate and brine
  2. customEvaporation of the
  3. dry with materialdried (magnesium sulfate) organic phase

Sources & evidence

ORD record
ord-5948503d575447fa92ec3af004b4141a
Source dataset
uspto-grants-1992_01
Patent number
US05081261

Reaction notes

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