Hydrazine hydrate (1:1) → HCID 57255716, compound

HRID 355539Notes

Reaction equation

HRID 355539 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([C@H:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:24])[CH2:11][N:12]1C(=O)C2=CC=CC=C2C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([C@H:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:24])[CH2:11][NH2:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10917643HCID 10917643, compound

Product 1

HCID 57255716HCID 57255716, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (2S)-3-phthalimido-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester (1.12 g), hydrazine monohydrate (612 mg) and ethanol (20 ml) was stirred at 25° C. for 17 hr. The reactant crystals were filtered off and the filtrate was evaporated. The residue was suspended in hexane and filtered. The filtrate was evaporated, and the residue was purified by silica-gel column chromatography (chloroform:methanol=40:1) to afford 642.2 mg of (2S)-3-amino-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester in colorless oil.

Workup

  1. filtrationThe reactant crystals were filtered off
  2. customthe filtrate was evaporated
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by silica-gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-0f9846efd9c7407d9990e3459711bab2
Source dataset
uspto-grants-1998_11
Patent number
US05831091

Reaction notes

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