Triethylamine → HCID 69588746, compound

HRID 1896989Notes

Reaction equation

HRID 1896989 reaction equation
[NH2:1][C@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([NH:5][CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37])([O-:29])=[O:28].C(N(CC)CC)C>C(Cl)Cl>[C:14]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][NH:5][C:3](=[O:4])[C@H:2]([NH:1][S:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N+:27]([O-:29])=[O:28])(=[O:37])=[O:38])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 69588123HCID 69588123, compound

Product 1

HCID 69588746HCID 69588746, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product of step 1 (12.3 g, 35.6 mmol) in methylene chloride (200 mL) was added 2-nitrobenzenesulfonyl chloride (9.00 g, 40.6 mmol) followed by triethylamine (6.4 mL, 46 mmol). After 30 minutes the reaction was concentrated and the residue partitioned between ethyl acetate and aqueous sodium 5 bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated. The resulting amber foam was purified by flash chromatography over silica (hexane/ethyl acetate) to afford 14.0 g (74%) of product as a colorless foam: 1H NMR (CDCl3) δ 7.95-7.87 (m, 1H), 7.76-7.62 (m, 3H), 7.35-7.15 (m, 10H), 7.06-6.94 (m, 3H), 6.90-6.83 (m, 2H), 6.42 (t, J=5.6, 1H), 5.80 (d, J=5.8, 1H), 4.12 (t, J=8.1, 1H), 4.01-3.82 (m, 3H), 3.18-3.08 (m, 1H), 2.68-3.57 (m, 1H) ppm.

Workup

  1. concentrationAfter 30 minutes the reaction was concentrated
  2. customthe residue partitioned between ethyl acetate and aqueous sodium 5 bicarbonate solution
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting amber foam was purified by flash chromatography over silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cf5d3fedceaa422ba9f60980c93b8137
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Reaction notes

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