Methanol → methyl (S)-2-amino-6-methyl-6-nitroheptanoate hydrochloride

HRID 1744023Notes

Reaction equation

HRID 1744023 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][C:9]([CH3:14])([N+:11]([O-:13])=[O:12])[CH3:10])[C:3]([OH:5])=[O:4].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][C:9]([CH3:14])([N+:11]([O-:13])=[O:12])[CH3:10])[C:3]([O:5][CH3:19])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 9834264(S)-2-amino-6-methyl-6-nitroheptanoic acid

Product 1

HCID 9813744methyl (S)-2-amino-6-methyl-6-nitroheptanoate hydrochloride

Procedure

(S)-2-Amino-6-methyl-6-nitroheptanoic acid (20.5 g) was dissolved in methanol (177 ml) and thionyl chloride (7.34 ml) was gently added dropwise under ice-cooling. The mixture was refluxed under heating for 2.5 h, and methanol was concentrated under reduced pressure to give the objective compound (21.9 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 2.5 h
  4. concentrationmethanol was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0e619d5f8ed486e98132525efb533ca
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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