Triethylamine → HCID 69588746, compound

HRID 1797125Notes

Reaction equation

HRID 1797125 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 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 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-76564d22a0624cb9912427d01a72db0b
Source dataset
uspto-grants-2006_04
Patent number
US07034031B2

Reaction notes

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