Methanol → HCID 131731853, compound

HRID 74768Notes

Reaction equation

HRID 74768 reaction equation
Cl.[NH2:2][CH:3]([CH:7]1[CH2:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:4]([OH:6])=[O:5].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[NH2:2][CH:3]([CH:7]1[CH2:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 131731852HCID 131731852, compound

Product 1

HCID 131731853HCID 131731853, compound

Procedure

To a mixture of #101 (195 mg, <0.913 mmol, 1 eq.) in methanol (20 mL, 0.04 M) was added thionyl chloride (0.666 mL, 9.13 mmol, 10 eq.). After two hours at reflux, the reaction mixture was concentrated in vacuo to give the single enantiomer #102 (175 mg, 84% over two steps) as a light-colored solid. LC-MS: m/z 192.3 [M+H+], retention time=0.80 minutes; GC-MS: m/z 192 [M+H+], retention time=3.206 minutes; 1H NMR (400 MHz, CD3OD) δ 7.24-7.33 (m, 2H), 7.11-7.18 (m, 2H), 4.40 (d, J=6.9 Hz, 1H), 3.99-4.05 (m, 1H), 3.78 (s, 3H), 3.46 (dd, J=14.8, 5.4 Hz, 1H), 3.23 (dd, J=14.8, 2.5 Hz, 1H).

Workup

  1. temperatureAfter two hours at reflux
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customto give the single enantiomer #102 (175 mg, 84% over two steps) as a light-colored solid

Sources & evidence

ORD record
ord-49f817a31ca74cdda0111b67a690024f
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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