4-Toluenesulfonyl chloride → HCID 86668483, compound

HRID 1944100Notes

Reaction equation

HRID 1944100 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:50][OH:51])[CH2:48][OH:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:52]1([CH3:62])[CH:57]=[CH:56][C:55]([S:58](Cl)(=[O:60])=[O:59])=[CH:54][CH:53]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:48][O:49][S:58]([C:55]1[CH:56]=[CH:57][C:52]([CH3:62])=[CH:53][CH:54]=1)(=[O:60])=[O:59])[CH2:50][OH:51])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 52914724HCID 52914724, compound

Product 1

HCID 86668483HCID 86668483, compoundYield 319.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol (Example 9, 500 mg, 0.70 mmol) in pyridine (15 mL) was added p-toluene sulfonyl chloride (670 mg, 0.21 mmol). After stirring for overnight at room temperature, reaction mixture was heated to 80° C. for another 18 h. The volatiles were evaporated, resulting residue was taken in ethyl acetate and washed with 1N HCl, brine, concentrated to furnish toluene-4-sulfonic acid (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-ylmethyl ester (580 mg). The crude product was used as such for next step without purification which also contains small amount of bis-tosylate.

Workup

  1. customreaction mixture
  2. temperaturewas heated to 80° C. for another 18 h
  3. customThe volatiles were evaporated
  4. customresulting residue
  5. washwashed with 1N HCl, brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-240e1322ffa64302acd2fb0355bdeede
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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