Hydrochloric Acid → Tert-butyl 4-benzyloxycarbonyl-alpha-phthalimido-1-thia-3-azaspiro[4.5]decane-2-acetate

HRID 372403Notes

Reaction equation

HRID 372403 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16]([O:20][C:21](=[O:47])[CH:22]([N:36]1[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]2[C:37]1=[O:46])[CH:23]1[NH:27][CH:26]([C:28]([OH:30])=[O:29])[C:25]2([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[S:24]1)([CH3:19])([CH3:18])[CH3:17].Cl>CN(C)C=O>[CH2:1]([O:30][C:28]([CH:26]1[C:25]2([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[S:24][CH:23]([CH:22]([N:36]2[C:40](=[O:41])[C:39]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]3[C:37]2=[O:46])[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:47])[NH:27]1)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 20327472Tert-butyl-4-carboxy-alphaphthalimido-1-thia-3-azaspiro[4.5]decane-2-acetate

Product 1

HCID 20327449Tert-butyl 4-benzyloxycarbonyl-alpha-phthalimido-1-thia-3-azaspiro[4.5]decane-2-acetateYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.5 g. (0.05 mole) of benzyl bromide are first added all at once and then 3.43 g. (0.034 mole) of triethylamine are added to a solution of 12 g. (0.026 mole) of tert-butyl-4-carboxy-alphaphthalimido-1-thia-3-azaspiro[4.5]decane-2-acetate in 130 ml. of anhydrous dimethylformamide. The reaction mixture is left to stand overnight at ambient temperature and then it is poured on to ice and 10 ml. of 6N hydrochloric acid are added followed by extraction with benzene. The organic phase is first washed with a 5% aqueous solution of sodium hydrogen carbonate and then with water, dried over anhydrous sodium sulfate, filtered and finally evaporated to dryness. After recrystallization from a mixture of diethyl ether and hexane (50/50), 12 g. (0.0215 mole) of tert-butyl 4-benzyloxycarbonyl-alpha-phthalimido-1-thia-3-azaspiro[4.5]decane-2-acetate are obtained. Yield: 82.7%. M.P. 165°-166° C.

Workup

  1. waitThe reaction mixture is left
  2. additionit is poured on to ice and 10 ml
  3. extractionfollowed by extraction with benzene
  4. washThe organic phase is first washed with a 5% aqueous solution of sodium hydrogen carbonate
  5. dry with materialwith water, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customfinally evaporated to dryness
  8. customAfter recrystallization
  9. additionfrom a mixture of diethyl ether and hexane (50/50), 12 g

Sources & evidence

ORD record
ord-a54b72a0d14046a0a14905978aa1d87a
Source dataset
uspto-grants-1978_05
Patent number
US04091027

Reaction notes

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