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

HRID 858963Notes

Reaction equation

HRID 858963 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-101ed5cc55ee471ba26e716df485ad96
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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