Triethylamine → (S)-[1-[[[(4-Methylphenyl)sulfonyl]amino]-carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, triethylammonium salt

HRID 279802Notes

Reaction equation

HRID 279802 reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][NH:3]1.[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18].[C:24]1([CH3:36])[CH:29]=[CH:28][C:27]([S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])=[CH:26][CH:25]=1>O1CCCC1>[CH2:17]([NH+:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:18].[CH3:36][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][C:34]([N:3]2[CH2:4][C@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:2]2=[O:1])=[O:35])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Product 1

HCID 131714656(S)-[1-[[[(4-Methylphenyl)sulfonyl]amino]-carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, triethylammonium salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-(2-Oxo-3-azetidinyl)carbamic acid, phenylmethyl ester (220 mgs) was dissolved in dry tetrahydrofuran (10 ml) and stirred well under nitrogen. Triethylamine (139 μl) was added, followed by p-toluenesulfonyl isocyanate (153 μl, 1 mmol). After 2 to 3 hours of stirring a crystalline material starts to precipitate out. After 2 hours of further stirring, the solid was removed by filtration, washed with a small volume of acetonitrile and dried in vacuo. Yield of the triethylamine salt is 332 mg, melting point 128°-130° C.

Workup

  1. stirringAfter 2 to 3 hours of stirring a crystalline material
  2. customto precipitate out
  3. customthe solid was removed by filtration
  4. washwashed with a small volume of acetonitrile
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b842d0502e814047a901ad949a636cab
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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