Hydrazine hydrate (1:1) → HCID 53989515, compound

HRID 2186503Notes

Reaction equation

HRID 2186503 reaction equation
[C:1]([NH:8][CH2:9][C@H:10]([OH:17])[CH2:11][C:12](OCC)=[O:13])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.[NH2:19][NH2:20]>CO>[C:1]([NH:8][CH2:9][C@H:10]([OH:17])[CH2:11][C:12]([NH:19][NH2:20])=[O:13])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54557405HCID 54557405, compound

Product 1

HCID 53989515HCID 53989515, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A 6.50 g (24.9 mmol) of ethyl (R)-4-hexanoylamino-3-hydroxybutyrate (optical purity: 95%e.e.) was dissolved in 26 ml of methanol, and 1.87 g (37.3 mmol) of hydrazine monohydrate was added thereto dropwise at room temperature. After the addition, the mixture was heated to 65° C. and then stirred for 2 hours. After the mixture was cooled to room temperature, stirring was conducted overnight to give 4.09 g (66%) of the title compound as a crystal. Melting point: 172.5° 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. stirringstirring
  5. waitwas conducted overnight

Sources & evidence

ORD record
ord-7d47d750a7d0427f86c27171adb5447d
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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