Methanol → Methyl 4-nitro-L-phenylalaninate hydrochloride

HRID 1820633Notes

Reaction equation

HRID 1820633 reaction equation
S(Cl)([Cl:3])=O.[NH:5](C(OC(C)(C)C)=O)[C@H:6]([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[CH3:27]O>>[ClH:3].[CH3:27][O:19][C:17](=[O:18])[C@H:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)[NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Procedure

1.49 ml of thionylchloride and 25 ml of methanol were mixed, cooled by dry-ice-acetonitrile bath and 2 g of Boc-Phe(4-NO2)—OH was added thereto. After stirring it for 1 hour and removing the bath, the solution was warmed up till room temperature and further stirred for 2.5 hours. The reaction solvent was concentrated under reduced pressure to obtain 1.83 g of the intended compound as white powder.

Workup

  1. temperaturecooled by dry-ice-acetonitrile bath
  2. customremoving the bath
  3. stirringfurther stirred for 2.5 hours
  4. concentrationThe reaction solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2990cc02df384165ab00aafccaf8350f
Source dataset
uspto-grants-2009_10
Patent number
US07605165B2

Reaction notes

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