Hydrazine hydrate (1:1) → HCID 86706769, compound

HRID 710056Notes

Reaction equation

HRID 710056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:6][CH2:7][C:8](=O)[C:9]#[C:10][C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O.[NH2:30][NH2:31]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:6][CH2:7][C:8]1[NH:31][N:30]=[C:10]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86706767(S)-t-Butyl 2-(4-(3,4-dimethoxyphenoxy)-3-oxobut-1-yn-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86706769HCID 86706769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH (10 mL) solution of the compound (395 mg) obtained in Example 14-(2), hydrazine hydrate (63 μL) was added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, water (50 mL) was added, and the organic layer extracted with AcOEt (50 mL) was dried (MgSO4), filtered and concentrated to give the titled compound (466 mg, pale brown amorphous.)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (50 mL) was added
  3. extractionthe organic layer extracted with AcOEt (50 mL)
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c08d4483652d4d1d99966dd5073ace3a
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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