o-Toluenesulfonyl chloride → HCID 178424421, compound

HRID 2099884Notes

Reaction equation

HRID 2099884 reaction equation
[C:1]([O:5][CH2:6][C@@:7]1([CH2:46][OH:47])[O:11][C@@:10]([SiH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[C@H:9]([OH:33])[C@@H:8]1[O:34][CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1)([CH3:4])([CH3:3])[CH3:2].[C:48]1([CH3:58])[C:49]([S:54](Cl)(=[O:56])=[O:55])=[CH:50][CH:51]=[CH:52][CH:53]=1.CCO[C:62]([CH3:64])=O>N1C=CC=CC=1.C(Cl)Cl>[C:1]([O:5][CH2:6][C@@:7]1([CH2:46][O:47][S:54]([C:49]2[C:62]([CH3:64])=[CH:51][CH:52]=[CH:53][CH:48]=2)(=[O:56])=[O:55])[O:11][C@@:10]([SiH:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[C@H:9]([O:33][S:54]([C:49]2[C:48]([CH3:58])=[CH:53][CH:52]=[CH:51][CH:50]=2)(=[O:56])=[O:55])[C@@H:8]1[O:34][CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8623o-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 131727553HCID 131727553, compound

Product 1

HCID 178424421HCID 178424421, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Dried Compound 46 (29.24 g, 44.79 mmol) was dissolved in a mixture of anhydrous pyridine (82 mL) and anhydrous CH2Cl2 (82 mL). To this solution was added toluenesulfonyl chloride (21.3 g, 112 mmol). After stirring at room temperature for 10 hours, the mixture was poured into EtOAc (1 L), washed with saturated aqueous NaHCO3 (2×0.8 L), then with 1% (v/v) aqueous AcOH (2×0.8 L). Dried over anhydrous Na2SO4, filtered, and evaporated to a brown oil. Purification by silica gel chromatography (2:1 hexanes:EtOAc) yielded Compound 47 (32.36 g, 75%) as a pale yellow foam.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×0.8 L)
  2. dry with materialDried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated to a brown oil
  5. customPurification by silica gel chromatography (2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-eee0c7a597094602b490cac6063a12a8
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

Loading…