Hydrazine hydrate (1:1) → HCID 53684831, compound

HRID 2186500Notes

Reaction equation

HRID 2186500 reaction equation
[C:1]([NH:4][CH2:5][C@H:6]([OH:13])[CH2:7][C:8](OCC)=[O:9])(=[O:3])[CH3:2].O.[NH2:15][NH2:16]>CO>[C:1]([NH:4][CH2:5][C@H:6]([OH:13])[CH2:7][C:8]([NH:15][NH2:16])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54306572HCID 54306572, compound

Product 1

HCID 53684831HCID 53684831, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A 5.00 g (26.4 mmol) of ethyl (R)-4-acetylamino-3-hydroxybutyrate (optical purity: 95%e.e.) was dissolved in 20 ml of methanol, and 2.00 g (39.6 mmol) of hydrazine monohydrate was added thereto dropwise at room temperature. After the addition, the mixture was heated to 65° C. and then stirred overnight. After the mixture was cooled to room temperature, 20 ml of methanol was added thereto and crystallization was carried out at 10° C. to give 3.90 g (84%) of the title compound. Melting point: 177.5° C. Optical purity: >99.9%e.e.

Workup

  1. customdropwise at room temperature
  2. additionAfter the addition
  3. temperatureAfter the mixture was cooled to room temperature
  4. customcrystallization
  5. customwas carried out at 10° C.

Sources & evidence

ORD record
ord-cd5ab9310a684347b410a27893751429
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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