Methanol → (S)-methyl 2-(methylamino)hex-5-enoate hydrochloride

HRID 501674Notes

Reaction equation

HRID 501674 reaction equation
S(Cl)([Cl:3])=O.C(O[C:10]([N:12](C)[C@@H:13]([CH2:17][CH2:18][CH:19]=[CH2:20])[C:14]([OH:16])=[O:15])=O)(C)(C)C.[CH3:22]O>>[ClH:3].[CH3:10][NH:12][C@@H:13]([CH2:17][CH2:18][CH:19]=[CH2:20])[C:14]([O:16][CH3:22])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86622313(S)-2-((tert-Butoxycarbonyl)(methyl)amino)hex-5-enoic acid

Product 1

HCID 86622315(S)-methyl 2-(methylamino)hex-5-enoate hydrochloride

Procedure

Step K (2): Thionyl chloride (1.22 mL, 16.9 mmol) was added to a round bottom flask charged with a solution of (S)-2-(tert-butoxycarbonyl(methyl)amino)hex-5-enoic acid (2.06 g, 8.47 mmol) from Step K (1) in MeOH at 0° C. After complete addition, heated at reflux for 2 h. Cooled to rt, concentrated in vacuo, and removed residuals on high vacuum overnight. This afforded 1.64 g (quantitative yield) of the title compound as an off-white solid. LC-MS (M+H)+=158.3; 1H NMR (500 MHz, CDCl3) δ ppm 2.09-2.27 (m, 3H) 2.29-2.43 (m, 1H) 2.71-2.81 (m, 3H) 3.77-3.88 (m, 3H) 5.04 (d, J=10.07 Hz, 1H) 5.12 (d, J=17.09 Hz, 1H) 5.68-5.82 (m, 1H) 9.59-9.72 (br s, 1H) 9.99-10.12 (br s, 1H).

Workup

  1. additionAfter complete addition
  2. temperatureheated
  3. temperatureat reflux for 2 h
  4. concentrationconcentrated in vacuo
  5. customremoved residuals on high vacuum overnight

Sources & evidence

ORD record
ord-12fd9ae83904498ea82fb5f1d86dd7e2
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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