Hydrazine hydrate (1:1) → 2-{[4-(3-Aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

HRID 914291Notes

Reaction equation

HRID 914291 reaction equation
[C:1]([O:5][C:6](=[O:30])[C:7]([CH3:29])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3=CC=CC=C3C2=O)[N:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6](=[O:30])[C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][NH2:18])[N:14]=1)([CH3:29])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 597588132-Methyl-2-{[4-(3-phthalimidopropyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

Product 1

HCID 597590072-{[4-(3-Aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-2-{[4-(3-phthalimidopropyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester (31.1 g) obtained in Example 32 was dissolved in ethanol (400 mL), hydrazine monohydrate (10 mL) was added, and the mixture was refluxed for 2 hr. The precipitated solid was removed by filtration, and the filtrate was concentrated under reduced pressure. Water and dichloromethane were added to the residue, and the organic layer was washed with water, and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give the title compound (20.1 g). The obtained compound was used in the next reaction without purification.

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. customThe precipitated solid was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater and dichloromethane were added to the residue
  5. washthe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6bafd0e3d75e438c9c43fae065e9bc71
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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