Hydrochloric Acid → HCID 23458748, compound

HRID 1680013Notes

Reaction equation

HRID 1680013 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[C:15]2([CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[S:14][CH:13]([CH:27]([N:35]2C(=O)C3=CC=CC=C3C2=O)[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.Cl.O>CN(C=O)C>[NH2:35][CH:27]([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([CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[S:14]1)[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 23458739HCID 23458739, compound

Product 1

HCID 23458748HCID 23458748, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

18.6 g (0.03 mole) of tert-butyl 4-benzyloxycarbonyl-8-phenyl-alpha-phthalimido-1-thia-3,8-diazaspiro[4.5]decane-2-acetate (obtained in 3.3) are suspended in 50 ml of N,N'-dimethylformamide. A solution containing 2 g (0.04 mole) of hydrazine hydrate in 20 ml of N,N-dimethylformamide is added dropwise at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm up to ambient temperature and stirred for 1 hour. The reaction mixture is then again cooled to 0° C. and slowly neutralized by the addition of 33.75 ml of 1N hydrochloric acid, whereafter it is stirred at ambient temperature for 2 hours after which time it solidifies. 300 ml of water are added, followed by extraction with chloroform. The organic phase is washed with water, dried with anhydrous sodium sulfate and evaporated to dryness. The residue is triturated with diethyl ether, filtered and the precipitate washed with diethyl ether. There are obtained 12.8 g of tert-butyl alpha-amino-4-benzyloxycarbonyl-8-phenyl-1 -thia-3,8-diazaspiro[4.5]decane-2-acetate.

Workup

  1. additionis added dropwise at 0° C. under an atmosphere of nitrogen
  2. temperatureThe reaction mixture is then again cooled to 0° C.
  3. stirringis stirred at ambient temperature for 2 hours after which time it
  4. extractionfollowed by extraction with chloroform
  5. washThe organic phase is washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue is triturated with diethyl ether
  9. filtrationfiltered
  10. washthe precipitate washed with diethyl ether

Sources & evidence

ORD record
ord-84f2146a018a47dcb9001d097d4ce36b
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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