Hydrazine hydrate (1:1) → HCID 178424420, compound

HRID 2099885Notes

Reaction equation

HRID 2099885 reaction equation
[C:1]([O:5][CH2:6][C@@:7]1([CH2:57][O:58][S:59]([C:62]2[C:63]([CH3:68])=[CH:64][CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[O:11][C@@:10]([SiH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[C@H:9]([O:33][N:34]2C(=O)C3=CC=CC=C3C2=O)[C@@H:8]1[O:45][CH2:46][C:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:50]=[CH:49][CH:48]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>CCO>[NH2:34][O:33][C@@H:9]1[C@H:8]([O:45][CH2:46][C:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:50]=[CH:49][CH:48]=2)[C@@:7]([CH2:57][O:58][S:59]([C:62]2[C:63]([CH3:68])=[CH:64][CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])([CH2:6][O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[O:11][C@@:10]1([SiH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178424419HCID 178424419, compound

Product 1

HCID 178424420HCID 178424420, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound 50 (15.9 g, 16.7 mmol) in anhydrous EtOH (500 mL) is added hydrazine hydrate (1.46 mL, 30.1 mmol). After stirring at room temperature for 3 hours, the mixture is concentrated in vacuo to ˜100 mL, then poured into EtOAc (500 mL) and washed with saturated aqueous NaHCO3 (2×100 mL). The organic phase is dried over anhydrous Na2SO4, filtered and evaporated. The crude Compound 51 is used without further purification

Workup

  1. concentrationthe mixture is concentrated in vacuo to ˜100 mL
  2. additionpoured into EtOAc (500 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×100 mL)
  4. dry with materialThe organic phase is dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude Compound 51 is used without further purification

Sources & evidence

ORD record
ord-9d7607bc63cf44659d6ddea8b6ebe452
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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