Hydrazine hydrate (1:1) → HCID 53854485, compound

HRID 2186494Notes

Reaction equation

HRID 2186494 reaction equation
[OH:1][C@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4](OC)=[O:5].O.[NH2:15][NH2:16]>CO>[OH:1][C@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4]([NH:15][NH2:16])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 6993014Methyl (3S)-3-hydroxy-3-phenylpropanoate

Product 1

HCID 53854485HCID 53854485, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

In a 1 liter four-necked flask were charged 200 g (1.11 mol) of methyl (S)-3-hydroxy-3-phenylpropionate (optical purity: 87%e.e.), 77.8 g (1.56 mol) of hydrazine monohydrate, and 400 ml of methanol, and the mixture was heated at 70° C. for 3 hours. The reaction mixture was cooled to 5° C. with ice-water, followed by filtration. The collected crystals were dissolved in 4.7 liter of methanol while hot and cooled to 5° C. The crystals thus precipitated were collected by filtration and dried to give 148 g (74%) of the title compound. Melting point: 179.5° C. Optical purity: >99.9%e.e.

Workup

  1. filtrationfollowed by filtration
  2. dissolutionThe collected crystals were dissolved in 4.7 liter of methanol while hot and
  3. temperaturecooled to 5° C
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-34ada7f8a70847bf8556453df6d9769e
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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