Triethylamine → HCID 136342840, compound

HRID 2292365Notes

Reaction equation

HRID 2292365 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.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].C(N(CC)CC)C.[OH:31][C:32]1[CH:33]=[C:34]([CH:39]=[N:40][NH:41]C(OC(C)(C)C)=O)[CH:35]=[CH:36][C:37]=1[OH:38]>C(OCC)(=O)C.ClCCl>[OH:31][C:32]1[CH:33]=[C:34]([CH:39]=[N:40][NH:41][S:18]([NH:21][C:22]([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:23])(=[O:20])=[O:19])[CH:35]=[CH:36][C:37]=1[OH:38]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 136040517HCID 136040517, compound

Product 1

HCID 136342840HCID 136342840, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6.61 g (30 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 90 ml of ethyl acetate was added 2.62 ml (30 mmol) chlorosulfonyl isocyanate, and the mixture was stirred for one hour at room temperature. After the addition of 45 ml of dichloromethane, the solution was cooled to 0° C., and 12.54 ml (90 mmol) of triethylamine was added, followed by solution A. The mixture was stirred over the weekend at room temperature and the precipitate filtered off by suction. To the filtrate were added 100 ml of ice water, and the mixture was washed two times with ethyl acetate. The aqueous phase was adjusted to pH 2 by adding 2N hydrochloric acid and extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was triturated with ether, filtered off by suction and dried in vacuo; yield: 5.58 g.

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. stirringThe mixture was stirred over the weekend at room temperature
  3. filtrationthe precipitate filtered off by suction
  4. additionTo the filtrate were added 100 ml of ice water
  5. washthe mixture was washed two times with ethyl acetate
  6. additionby adding 2N hydrochloric acid
  7. extractionextracted three times with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was triturated with ether
  12. filtrationfiltered off by suction
  13. customdried in vacuo

Sources & evidence

ORD record
ord-eb0dff6d35bc4c8d821e96ebee85cf8d
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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