Benzyl Bromide → HCID 23458739, compound

HRID 1680011Notes

Reaction equation

HRID 1680011 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH:12]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[S:15][CH:14]([CH:28]([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:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[NH:13]1)([OH:11])=[O:10]>CN(C)C=O>[CH2:1]([O:11][C:9]([CH:12]1[C:16]2([CH2:17][CH2:18][N:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]2)[S:15][CH:14]([CH:28]([N:36]2[C:37](=[O:46])[C:38]3=[CH:45][CH:44]=[CH:43][CH:42]=[C:39]3[C:40]2=[O:41])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[NH:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 23458754HCID 23458754, compound

Product 1

HCID 23458739HCID 23458739, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

17 g (0.10 mole) of benzyl bromide, dissolved in 20 ml of N,N-dimethylformamide are added to 24 g (0.0447 mole) of the alpha-isomer of tert-butyl 4-carboxy-8-phenyl-alpha-phthalimido-1-thia-3,8-diazaspiro[4.5]decane-2-acetate, obtained in 2.3, dissolved in 200 ml of N,N-dimethylformamide. The reaction mixture is stirred overnight at ambient temperature and is then poured onto ice, extracted three times with 500 ml amounts of ethyl acetate and the organic phase washed successively with a little water, with a saturated aqueous solution of sodium hydrogen carbonate and again with a little water. The solution is then dried and evaporated to dryness. After recrystallization from ethyl acetate, there are obtained 18.8 g tert-butyl 4-benzyloxycarbonyl-8-phenyl-alpha-phthalimido-1-thia-3,8-diazaspiro[4.5]decane-2-acetate. Yield: 66%; M.P. 184°-185° C.

Workup

  1. customobtained in 2.3
  2. additionis then poured onto ice
  3. extractionextracted three times with 500 ml amounts of ethyl acetate
  4. washthe organic phase washed successively with a little water, with a saturated aqueous solution of sodium hydrogen carbonate and again with a little water
  5. customThe solution is then dried
  6. customevaporated to dryness
  7. customAfter recrystallization from ethyl acetate, there

Sources & evidence

ORD record
ord-a0960830dca74a40a6c683a5f03f1356
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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