2-Nitrobenzenesulfonyl chloride → HCID 131733848, compound

HRID 708537Notes

Reaction equation

HRID 708537 reaction equation
[NH2:1][CH2:2][C:3]1[C:7]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][N:5]([CH2:27][C@@H:28]2[C@H:31]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30](=[O:43])[N:29]2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[N:4]=1.[N+:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[S:64](Cl)(=[O:66])=[O:65])([O-:57])=[O:56]>C(Cl)Cl>[Si:10]([O:9][CH2:8][C:7]1[C:3]([CH2:2][NH:1][S:64]([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=2[N+:55]([O-:57])=[O:56])(=[O:65])=[O:66])=[N:4][N:5]([CH2:27][C@@H:28]2[C@H:31]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30](=[O:43])[N:29]2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[N:6]=1)([C:23]([CH3:24])([CH3:25])[CH3:26])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 131733849HCID 131733849, compound

Product 1

HCID 131733848HCID 131733848, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(aminomethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate (234 mg, 0.312 mmol) in DCM (3.1 mL) at 0° C. was added 2-nitrobenzene-1-sulfonyl chloride (77.2 mg, 0.338 mmol) followed by TEA (87 μL, 0.62 mmol). After 2.2 h of stirring at rt, it was diluted with DCM and washed with KHSO4 (2%, aq). The aqueous layer was extracted with DCM (3×) and the combined organic layers were washed with brine, dried over Na2SO4 and concd in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-60%), affording the title compound (252 mg, 87%) as an off-white solid. Rt=1.24 min, m/z=934.4 (M+1) Method 2m_acidic.

Workup

  1. washwashed with KHSO4 (2%, aq)
  2. extractionThe aqueous layer was extracted with DCM (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4 and concd in vacuo
  5. customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-60%)

Sources & evidence

ORD record
ord-30aed02595ec4f278ea8a17da68d4b8b
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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