Benzenesulfonyl chloride → HCID 59784109, compound

HRID 2079765Notes

Reaction equation

HRID 2079765 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:39])[C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C@H:21]1[C:26]([NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:27])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CCN(C(C)C)C(C)C.[C:49]1([S:55](Cl)(=[O:57])=[O:56])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(Cl)Cl>[CH3:1][N:2]([C@@H:10]([CH3:39])[C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:55]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)(=[O:57])=[O:56])[CH2:22][C@H:21]1[C:26]([NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:27])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[C:3](=[O:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59784098HCID 59784098, compound

Product 1

HCID 59784109HCID 59784109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Intermediate 7 (200 mg, 0.37 mmol) is dissolved in dry CH2Cl2 (4 mL) and the flask sealed under N2. DIEA (96 μL, 0.56 mmol) is added, followed by benzenesulfonyl chloride (46 μL, 0.36 mmol), then the mixture stirred at RT for 2 h. The reaction is subsequently diluted with CH2Cl2 (50 mL) and washed with sat. NaHCO3 (50 mL), brine (50 mL) and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure to afford an oil which is purified by flash chromatography on silica gel (25% Et2O/CH2Cl2). The title compound is isolated as a colourless glass (216 mg, 86% yield): 1H NMR δ (CDCl3) 7.51-7.86 (m, 5H), 7.03-7.25 (m, 4H), 6.69 (v br s, 1H), 6.04 (br d, J=8.2 Hz, 1H), 5.16-5.25 (m, 1H), 4.29-4.75 (br m, 3H), 3.47-4.21 (br m, 3H), 2.69-2.88 (br m, 5H), 2.38-2.67 (m, 2H), 1.81-2.09 (m, 5H), 1.55 (s, 3H), 1.46 (s, 9H), 1.23-1.31 (br m, 2H), 0.84-0.92 (br m, 3H), 0.76 (d, J=6.7 Hz, 2H); LCMS (APCl+) 685.6 (MH+, 100%).

Workup

  1. customthe flask sealed under N2
  2. washwashed with sat. NaHCO3 (50 mL), brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationAfter filtration
  5. customthe solvent is removed under reduced pressure
  6. customto afford an oil which
  7. customis purified by flash chromatography on silica gel (25% Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-8dee5e6ab7b249b8965b613be134bd13
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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