Methanesulfonyl chloride → HCID 131733796, compound

HRID 708462Notes

Reaction equation

HRID 708462 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[CH:22](O)[CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[CH:22]=[CH:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:19]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 118379551HCID 118379551, compound

Product 1

HCID 131733796HCID 131733796, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxoazetidin-2-yl)methyl)-4-hydroxy-2-oxoimidazolidine-1-carboxylate (160 mg, 0.368 mmol) in DCM (5 mL) at 0° C. was added methanesulfonyl chloride (31 μL, 0.41 mmol) followed by TEA (0.15 mL, 1.1 mmol). After stirring for 1 h at 0° C., the solution was concentrated in vacuo and purified via silica gel chromatography (MeOH-DCM, 2-5%), affording the title compound (100 mg, 65%). LCMS: m/z=415.1 (M−1); 1H NMR (400 MHz, CDCl3): δ 8.02 (s, 1H), 7.41-7.27 (m, 5H), 7.06 (d, J=8.4 Hz, 1H), 6.61 (d, J=3.2 Hz, 1H), 6.15 (d, J=3.2 Hz, 1H), 5.21-5.09 (m, 3H), 4.30 (dd, J=14.4, 9.6 Hz, 1H), 4.01-3.94 (m, 1H), 3.49 (dd, J=14.8, 3.2 Hz, 1H), 1.46 (s, 9H).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified via silica gel chromatography (MeOH-DCM, 2-5%)

Sources & evidence

ORD record
ord-8d1af956a0f84603bd0250be003b633b
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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