Potassium tert-butoxide → HCID 89561383, compound

HRID 1747228Notes

Reaction equation

HRID 1747228 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([CH2:16][OH:17])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1)=[O:4].CC([O-])(C)C.[K+]>C1COCC1>[I:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][C:6]1([CH3:15])[NH:5][C:3](=[O:4])[CH2:2][O:17][CH2:16]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 118117511HCID 118117511, compound

Product 1

HCID 89561383HCID 89561383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of rac-2-chloro-N-[1-hydroxymethyl-2-(3-iodo-phenyl)-1-methyl-ethyl]-acetamide H-7 (1.0 g, 2.7 mmol) in THF (13 mL) was added dropwise to a RT solution of KOtBu (6.8 mL, 6.8 mmol, 1M soln. in THF) under argon and the reaction mixture was stirred for 20 min. The reaction was quenched with 1M aq. HCl, diluted with water and concentrated in vacuo. The remaining aqueous phase was extracted with DCM (3×) and the combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo to give the title compound that was used further without purification. LC-MS A: tR=0.75 min; [M+H+MeCN]+=373.02.

Workup

  1. customThe reaction was quenched with 1M aq. HCl
  2. additiondiluted with water
  3. concentrationconcentrated in vacuo
  4. extractionThe remaining aqueous phase was extracted with DCM (3×)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2adfc539f6f4453baba915bc8d2a1b18
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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