Triethylamine → HCID 86709275, compound

HRID 517293Notes

Reaction equation

HRID 517293 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][NH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:19]1([CH2:25][S:26](Cl)(=[O:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC(OC)(C)C>O1CCCC1.CC(C)=O.CCCCCCC>[Si:1]([O:8][CH2:9][CH2:10][NH:11][S:26]([CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:28])=[O:27])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 74740Phenylmethanesulfonyl chlorideHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilane

Product 1

HCID 86709275HCID 86709275, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0° C. was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N.HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel column chromatography (0-30% Acetone in heptane, 216 nM) to N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenylmethanesulfonamide (17.8 g, 81% yield). LCMS (ESI), m/z, 330. [M+H]+.

Workup

  1. customat 0° C.
  2. customthe Et3N.HCl salt was removed by filtration
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-5b5e989777d84b4b982eea0d3cfdc8af
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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