Formic Acid → Norleucine hydrochloride

HRID 224954Notes

Reaction equation

HRID 224954 reaction equation
C[O:2][C:3](=[O:14])[CH:4]([NH:9]C(OC)=O)[CH2:5][CH2:6][CH2:7][CH3:8].[ClH:15].C(O)=O>O>[ClH:15].[NH2:9][CH:4]([C:3]([OH:14])=[O:2])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 536557612-Methoxycarbonylaminohexanoic acid methyl ester

Product 1

HCID 17985082Norleucine hydrochlorideYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.07 grams of 2-methoxycarbonylaminohexanoic acid methyl ester were heated in 15 ml of a mixture consisting of equal parts of concentrated hydrochloric acid, 100 weight percent formic acid and water for 24 hours under reflux. The acid mixture was removed in a vacuum, the oily residue treated twice with 20 ml of acetone and freed from acetone again in a vacuum. The now crystalline residue was intensively stirred with 10 ml of acetone, filtered with suction and dried over diphosphorus pentoxide. There were obtained 3.26 grams (97.3%) of D,L-norleucine hydrochloride pure by thin layer chromatography.

Workup

  1. temperatureunder reflux
  2. customThe acid mixture was removed in a vacuum
  3. additionthe oily residue treated twice with 20 ml of acetone
  4. filtrationfiltered with suction
  5. dry with materialdried over diphosphorus pentoxide

Sources & evidence

ORD record
ord-b4d671eedc4d4d609646148a8645eb0a
Source dataset
uspto-grants-1980_11
Patent number
US04234744

Reaction notes

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