4-Toluenesulfonyl chloride → (S)-2-(Benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate

HRID 1887386

Reaction equation

HRID 1887386 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.[O:12]1[CH2:16][CH:15]=[CH:14][C@H:13]1[C@@H:17]([OH:30])[CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.O>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:30][C@H:17]([C@@H:13]2[CH:14]=[CH:15][CH2:16][O:12]2)[CH2:18][NH:19][C:20]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:29])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59343386Benzyl (S)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate

Product 1

HCID 59343388(S)-2-(Benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of p-toluenesulfonyl chloride (760 mg, 3.99 mmol) in pyridine (10.0 mL), alcohol (17) (600 mg, 2.28 mmol) was stirred at 40° C. for a total of 6 hours and stood at 24° C. for 16 hours then diluted with water (20 mL). The product was extracted into tert-butyl methyl ether (2×50 mL) then dried (MgSO4), filtered and reduced in vacuo. Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 10:90 to 30:70 gave tosylate (32) (789 mg, 83%) as a white solid.

Workup

  1. extractionThe product was extracted into tert-butyl methyl ether (2×50 mL)
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. washFlash chromatography over silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-d4661608fcf140eebdd49ec5a18e7691
Source dataset
uspto-grants-2013_08
Patent number
US08501744B2

Linked notes

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