Water → HCID 22749578, compound

HRID 2163825Notes

Reaction equation

HRID 2163825 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][O:19][CH2:18][CH2:17]2)[S:15][CH:14]([CH:22]([N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:13]1)([OH:11])=[O:10].C(N(CC)CC)C.O>CN(C)C=O>[CH2:1]([O:11][C:9]([CH:12]1[C:16]2([CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:15][CH:14]([CH:22]([N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[NH:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 22749602HCID 22749602, compound

Product 1

HCID 22749578HCID 22749578, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.3 g (0.019 mole) of benzyl bromide are added all at once to a solution of 4.62 g (0.01 mole) of the alpha isomer of tert-butyl 4-carboxy-alphaphthalimido-8-oxa-1-thia-3-azaspiro[4.5]decane-2-acetate in 50 ml of dimethylformamide, and then, over a period of 20 minutes, 1.32 g (0.013 mole) of triethylamine in 5 ml of dimethylformamide are added. The reaction mixture is gently stirred overnight at ambient temperature. The clear solution thus obtained is poured into a mixture of ice and water and then extracted with benzene. After washing the organic phase with a 5% aqueous solution of sodium hydrogen carbonate and then with water, it is evaporated to dryness. The residue obtained is recrystallized from diethyl ether to give 4.7 g (0.00085 mole) of tert-butyl 4-benzyloxycarbonyl-alpha-phthalimido-8-oxa-1-thia-3-azaspiro[4.5]decane-2-acetate (yield: 85.2% of theory); M.P. 168-169° C. Another synthesis with quantities 10 times larger gave a yield of 93.6% of theory.

Workup

  1. waitThe reaction mixture is gently stirred overnight at ambient temperature
  2. customThe clear solution thus obtained
  3. extractionextracted with benzene
  4. washAfter washing the organic phase with a 5% aqueous solution of sodium hydrogen carbonate
  5. customwith water, it is evaporated to dryness
  6. customThe residue obtained
  7. customis recrystallized from diethyl ether

Sources & evidence

ORD record
ord-fbfc755125ac430891c5543ea4b7e58c
Source dataset
uspto-grants-1979_01
Patent number
US04137236

Reaction notes

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