Methanol → HCID 14732250, compound

HRID 501670Notes

Reaction equation

HRID 501670 reaction equation
S(Cl)([Cl:3])=O.C(O[C:10]([N:12](C)[C@@H:13]([CH2:17][CH:18]=[CH2:19])[C:14]([OH:16])=[O:15])=O)(C)(C)C.[CH3:21]O>>[ClH:3].[CH3:10][NH:12][C@@H:13]([CH2:17][CH:18]=[CH2:19])[C:14]([O:16][CH3:21])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15689339HCID 15689339, compound

Product 1

HCID 14732250HCID 14732250, compound

Procedure

Step G (1): Thionyl chloride (1.7 g, 14.4 mmol) was added to a round bottom flask charged with a solution of (S)-2-(tert-butoxycarbonyl(methyl)-amino)pent-4-enoic acid (1.66 g, 7.2 mmol) [Tetrahedron (1991), 47(29), pp. 5453-62] in MeOH at 0° C. After complete addition, the reaction mixture was heated at reflux for 2 h, then cooled to rt. The resulting solution was concentrated in vacuo and the residual volatiles were removed on high vacuum overnight to afford 1.32 g (quantitative yield) of the title compound as an off-white solid. LC-MS (M+H)+=143.96; [α]D +3.7 (c=7.57 mg/mL, methanol); 1H NMR (500 MHz, CD3OD) δ ppm 2.71-2.84 (m, 5H) 3.88 (s, 2H) 4.19 (t, J=5.65 Hz, 1H) 4.84 (s, 2H) 5.26-5.38 (m, 1H) 5.68-5.83 (m, 1H).

Workup

  1. customat 0° C
  2. additionAfter complete addition
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 2 h
  5. concentrationThe resulting solution was concentrated in vacuo
  6. customthe residual volatiles were removed on high vacuum overnight

Sources & evidence

ORD record
ord-cd6b689997914461b868610a74823141
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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