Chlorosulfonyl isocyanate → HCID 86742712, compound

HRID 2292374Notes

Reaction equation

HRID 2292374 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[Si](C)(C)[O:26][C:27]1[CH:28]=[C:29]([N:38]2[CH2:42][CH2:41][N:40]([Si](C)(C)C)[C:39]2=[O:47])[CH:30]=[CH:31][C:32]=1[O:33][Si](C)(C)C>C(OCC)(=O)C>[OH:26][C:27]1[CH:28]=[C:29]([N:38]2[CH2:42][CH2:41][N:40]([S:18]([NH:21][C:22]([N:3]3[CH2:4][C@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:2]3=[O:1])=[O:23])(=[O:20])=[O:19])[C:39]2=[O:47])[CH:30]=[CH:31][C:32]=1[OH:33]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 21277154HCID 21277154, compound

Product 1

HCID 86742712HCID 86742712, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 3.9 g (17.8 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 30 ml of ethyl acetate was added 2.5 g (17.8 mmol) of chlorosulfonyl isocyanate. The reaction mixture was stirred for one hour at room temperature and a solution of 7.14 g (17.8 mmol) of 1-[3,4-bis[(trimethylsilyl)oxy]phenyl]-3-(trimethylsilyl)-2-imidazolidinone in 30 ml of ethyl acetate was added dropwise. After stirring overnight at room temperature, the mixture was washed with brine, dried over sodium sulfate and evaporated in vacuo; yield: 8.46 g.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washthe mixture was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e586551ab007452687957cdac4d9d8ed
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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