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

HRID 432995Notes

Reaction equation

HRID 432995 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-2afc4d03de2d4a8e9a7cf04e515001fb
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

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