4-Toluenesulfonyl chloride → HCID 86738250, compound

HRID 1447053Notes

Reaction equation

HRID 1447053 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:50])[CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@@H:21]1[C@@H:25](/[CH:26]=[CH:27]/[C@@H:28]([O:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[CH:29]([CH3:34])[CH2:30][C:31]#[C:32][CH3:33])[C@H:24]([O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)[CH2:23][C@@H:22]1[OH:49].[N+](=C)=[N-].C(=O)(O)[O-].[Na+].S(C1C=CC(C)=CC=1)([O-])(=O)=O>CCOCC.O.N1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:50])[CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@@H:21]1[C@@H:25](/[CH:26]=[CH:27]/[C@@H:28]([O:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[CH:29]([CH3:34])[CH2:30][C:31]#[C:32][CH3:33])[C@H:24]([O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)[CH2:23][C@@H:22]1[O:49][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

9

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 9550DiazomethaneHCID 85570p-ToluenesulfonateHCID 516892Sodium BicarbonateHCID 70549039HCID 70549039, compound

Product 1

HCID 86738250HCID 86738250, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

At 0°, 2.15 g. of p-toluenesulfonyl chloride is addded to a solution of 3.05 g. of (5Z,13E)-(9S,11R,15S,16RS)-11,15-bis(tetrahydropyran-2-yloxy)-9-hydroxy-16-methyl-5,13-prostadien-18-ynoic acid methyl ester (prepared from the corresponding acid with ethereal diazomethane solution) in 6 ml. of pyridine, agitated for 6 hours at room temperature and then allowed to stand for 60 hours at 5°. The mixture is then diluted with ether, shaken in succession once with water, once with ice-cold 3% sulfuric acid, once with water, once with 5% sodium bicarbonate solution, twice with water, and dried over magnesium sulfate and evaporated under vacuum, thus obtaining 3.7 g. of the tosylate as a colorless oil.

Workup

  1. customAt 0°
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under vacuum
  4. customthus obtaining 3.7 g

Sources & evidence

ORD record
ord-bafc3f9b1beb4237a42166841a16c62b
Source dataset
uspto-grants-1982_02
Patent number
US04315013

Reaction notes

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