Pyridine → tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

HRID 2075415Notes

Reaction equation

HRID 2075415 reaction equation
[S:1](Cl)(Cl)=[O:2].[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)[C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][OH:16])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].N1C=CC=CC=1>CC#N.C(Cl)Cl.C1COCC1>[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=1)[C@H:14]1[CH2:15][O:16][S:1](=[O:2])[N:17]1[C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:7])[CH3:6]

Participants

7

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86636682tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 67089512tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxideYield 90%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thionyl chloride (0.74 mL, 10.1 mmol) in MeCN (12 mL) and DCM (12 mL) at −78° C. was added a solution of tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (1.82 g, 4.05 mmol) in MeCN (20 mL), DCM (20 mL) and THF (4 mL) dropwise via a dropping funnel. After 10 minutes, pyridine (1.82 mL, 22.3 mmol) was added dropwise at −78° C. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo. The residue was taken up in EtOAc (60 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane) to provide the product as a white solid (1.80 g, 90%).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane)

Sources & evidence

ORD record
ord-cd11a6131eb14f6ca856fa22fb907999
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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