Hydrochloric Acid → Ethyl 2-acetamido-3-aminobutyrate

HRID 1981643Notes

Reaction equation

HRID 1981643 reaction equation
[C:1]([NH:4][C:5](=[C:11]([NH2:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C([BH3-])#N.[Na+].Cl>CO.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2>[C:1]([NH:4][CH:5]([CH:11]([NH2:13])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 86740825Ethyl 2-acetamido-3-aminobut-2-enoate

Product 1

HCID 23319786Ethyl 2-acetamido-3-aminobutyrate

Reagents, catalysts & solvents 2

HCID 6451Bromocresol GreenCatalystHCID 887MethanolSolvent

Procedure

After dispersing 0.043 mol of ethyl 2-acetamido-3-aminobut-2-enoate in 25 ml of methanol together with 0.043 mol of sodium cyanoborohydride and a few drops of 0.04% bromcresol green indicator, the reaction mixture was cooled in ice, and 2M methanolic hydrochloric acid was added until the yellow color stabilized. The ice bath was removed, and the reaction was stirred for two hours, after which the solvent was removed and the reaction mixture worked up to provide ethyl 2-acetamido-3-aminobutyrate as a slightly greenish oil containing a 2.5/1 molar ratio of threo and erythro diastereomers.

Workup

  1. temperaturethe reaction mixture was cooled in ice
  2. customThe ice bath was removed
  3. customafter which the solvent was removed

Sources & evidence

ORD record
ord-ece12c110bd44841bda7abc2be3e4784
Source dataset
uspto-grants-1986_06
Patent number
US04593118

Reaction notes

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