Hydrazine hydrate (1:1) → HCID 23458740, compound

HRID 1680012Notes

Reaction equation

HRID 1680012 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[C:15]2([CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[S:14][CH:13]([CH:22]([N:30]2C(=O)C3=CC=CC=C3C2=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>O1CCOCC1.C1(CO)C=CC=CC=1>[NH2:30][CH:22]([CH:13]1[NH:12][CH:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C:15]2([CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[S:14]1)[C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 23458717HCID 23458717, compound

Product 1

HCID 23458740HCID 23458740, compound

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 113.2 g (0.2 mole) of tert-butyl 4-benzyloxycarbonyl-8-methyl-alpha-phthalimido-1-thia-3,8-diazaspiro[4.5]decane-2-acetate (obtained in 3.1) in 730 ml of dioxan are added 13.4 g of hydrazine hydrate. After 24 hours, a further 6 g of hydrazine hydrate are added, followed by filtration after 24 hours. The mixture is evaporated and the residue is dissolved in 1 liter of benzene, then filtered after 24 hours and the new residue obtained by evaporation is passed through a column of silica gel (60 Merck), using a 91 v/v benzene-methanol mixture as eluent. In this way, a solution of tert-butyl alpha-amino-4-benzyloxycarbonyl-8-methyl-1-thia-3,8-diazaspiro[4.5]decane-2-acetate is obtained, which is subjected as much to step 5.1.

Workup

  1. filtrationfollowed by filtration after 24 hours
  2. customThe mixture is evaporated
  3. dissolutionthe residue is dissolved in 1 liter of benzene
  4. filtrationfiltered after 24 hours
  5. customthe new residue obtained by evaporation

Sources & evidence

ORD record
ord-32f00999019d4d36a4d35f09ad45e1b7
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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