Chlorosulfonyl isocyanate → HCID 14326680, compound

HRID 2292341Notes

Reaction equation

HRID 2292341 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:17][S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19]>C(OCC)(=O)C>[Cl:17][S:18]([NH:21][C:22]([N:3]1[CH2:4][C@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2]1=[O:1])=[O:23])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Product 1

HCID 14326680HCID 14326680, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6.61 g (0.030 mol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 240 ml of dry ethyl acetate, 2.62 ml (0.030 mol) of chlorosulfonyl isocyanate was added and the mixture was stirred for 1 hour at room temperature to form a solution of (S)-[1-[[(chlorosulfonyl)amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester. After cooling to 0° C., a solution of 12.54 ml (0.090 mol) of triethylamine in 60 ml of dry dichloromethane was dropped in, followed by the dropwise addition of the freshly prepared solution A (0° C.). Overnight the mixture was stirred well at room temperature, then poured into ice water and acidified to pH 2 by the addition of 1N hydrochloric acid. The two phases was separated and the aqueous phase was extracted twice with ethyl acetate. 200 ml of ice water were added to the combined organic phases and the pH of the mixture was adjusted to pH 6.5 by the addition of 1N sodium hydroxide. The aqueous phase was separated, washed again with ethyl acetate, concentrated in vacuo and finally freeze dried; yield: 13.11 g.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-32039b1426644f95a1748fde93da4fbb
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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