p-Bromobenzenesulfonyl chloride → HCID 86642249, compound

HRID 1517174Notes

Reaction equation

HRID 1517174 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N2CCN(CC2)C1.[Br:44][C:45]1[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>C1(C)C=CC=CC=1>[Br:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([O:28][C@@H:26]2[CH2:25][N:22]3[C:23](=[O:24])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C@@H:17]4[CH2:30][C@@:18]4([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:19][C:20](=[O:29])[C@@H:21]3[CH2:27]2)(=[O:53])=[O:52])=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 9237DabcoHCID 57384485HCID 57384485, compound

Product 1

HCID 86642249HCID 86642249, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of (2S,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (22.1 g, 44.8 mmol) and DABCO (8.5 g, 76.7 mmol) in toluene (88 mL) may be stirred at room temperature. To this solution may be added a solution of 4-bromobenzene-1-sulfonyl chloride 17.2 g, 67.2 mmol) in toluene (44 mL). After the addition is complete the reaction mixture can be quenched with 10% aqueous sodium carbonate (110 mL) and the mixture stirred for 15 min. Tetrahydrofuran (44 mL) can be added and the mixture is washed with 0.5 M HCl, water, and then saturated aqueous sodium chloride. The organic layer may be dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure and dried to provide the title compound (27.7 g, 87% yield), which may be used without further purification.

Workup

  1. additionAfter the addition
  2. customcan be quenched with 10% aqueous sodium carbonate (110 mL)
  3. additionTetrahydrofuran (44 mL) can be added
  4. washthe mixture is washed with 0.5 M HCl, water
  5. dry with materialThe organic layer may be dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-a21b6d3b66794b61bbb9cd10eb5744fd
Source dataset
uspto-grants-2012_07
Patent number
US08232246B2

Reaction notes

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