Chlorosulfonyl isocyanate → HCID 86741567, compound

HRID 652212Notes

Reaction equation

HRID 652212 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]2[CH2:15][NH:14][C:13]2=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][N:36]([C:39](=[O:41])[NH2:40])[C:35]1=[O:42])=[O:30])([CH3:27])([CH3:26])[CH3:25].[K]>O1CCCC1.C(N(CC)CC)C>[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][N:36]([C:39]([NH:40][S:18]([NH:21][C:22]([N:14]2[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:13]2=[O:16])=[O:23])(=[O:20])=[O:19])=[O:41])[C:35]1=[O:42])=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 70918Chlorosulfonyl isocyanateHCID 5462222PotassiumHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 21277202HCID 21277202, compound

Product 1

HCID 86741567HCID 86741567, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-70 °C

Procedure

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2azetidinone (2 g) was suspended in 200 ml of dry tetrahydrofuran and cooled to -70° C. Chlorosulfonylisocyanate (1.4 g) dissolved in 7 ml of dry tetrahydrofuran was added with stirring. The temperature was allowed to rise to 0° C. and this temperature was maintained for 10 minutes. Afterwards it was cooled to -40° C., 1.2 g of triethylamine was dropped in and 2.9 g of 1-[2-[(t-butoxycarbonyl)amino]ethyl]-3-carbamoyl-2-oxoimidazolidine was added. This mixture was stirred at room temperature for 14 hours. Following the work-up procedure described in example 34A yielded 5.4 g of (S)-[1-[[[[[[3-[2-(t-butoxycarbonylamino)ethyl]-2-oxo-1-imidazolidinyl]carbonyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3azetidinyl]carbamic acid, phenylmethyl ester, potassium salt.

Workup

  1. additionwas added
  2. customto rise to 0° C.
  3. temperaturethis temperature was maintained for 10 minutes
  4. temperatureAfterwards it was cooled to -40° C.
  5. additionwas added
  6. stirringThis mixture was stirred at room temperature for 14 hours

Sources & evidence

ORD record
ord-c73de209473c47a59744800481333009
Source dataset
uspto-grants-1987_06
Patent number
US04670553

Reaction notes

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