4-Nitrobenzenesulfonyl chloride → HCID 86708056, compound

HRID 1524353Notes

Reaction equation

HRID 1524353 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([NH:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:21][CH2:22][CH:23]([F:47])[CH2:24][NH:25][C:26](=[O:46])[C@H:27]([CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:28][C:29]([O:31][CH3:32])=[O:30])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N+:63]([C:66]1[CH:71]=[CH:70][C:69]([S:72](Cl)(=[O:74])=[O:73])=[CH:68][CH:67]=1)([O-:65])=[O:64]>ClCCl>[Si:1]([O:18][CH2:19][C@@H:20]([N:48]([CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[S:72]([C:69]1[CH:68]=[CH:67][C:66]([N+:63]([O-:65])=[O:64])=[CH:71][CH:70]=1)(=[O:73])=[O:74])[CH2:21][CH2:22][CH:23]([F:47])[CH2:24][NH:25][C:26](=[O:46])[C@H:27]([CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[NH:28][C:29]([O:31][CH3:32])=[O:30])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 86708055HCID 86708055, compound

Product 1

HCID 86708056HCID 86708056, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the material from Step 12 (85 mg, 0.12 mmol) in dichloromethane (1.1 mL) were added N,N-diisopropylethylamine (30 μL, 0.172 mmol) and 4-nitrobenzenesulfonyl chloride (28 mg, 0.126 mmol). The reaction mixture was stirred at room temperature overnight. Additional N,N-diisopropylethylamine (30 μL, 0.172 mmol) and 4-nitrobenzenesulfonyl chloride (6 mg, 0.03 mmol) were added, stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 85 mg of the title compound. LCMS (M+1)=947

Workup

  1. stirringstirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-aed245048bb448b68d7ad0437806a6b0
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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