Hydrazine hydrate (1:1) → HCID 54088444, compound

HRID 2186504Notes

Reaction equation

HRID 2186504 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([OH:17])[CH2:11][C:12](OCC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:19][NH2:20]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([OH:17])[CH2:11][C:12]([NH:19][NH2:20])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53755420HCID 53755420, compound

Product 1

HCID 54088444HCID 54088444, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A 6.50 g (26.1 mmol) of ethyl (R)-4-t-butoxycarbonylamino-3-hydroxybutyrate (optical purity: 95%e.e.) was dissolved in 26 ml of methanol, and 1.96 g (39.1 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 5 hours. After the mixture was cooled to room temperature, stirring was conducted overnight to give 4.27 g (70%) of the title compound. Melting point: 143.6° 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-73dbf7fa41514e29ac2b31984a93ccd4
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

Loading…