4-Toluenesulfonyl chloride → HCID 86598920, compound

HRID 456768Notes

Reaction equation

HRID 456768 reaction equation
[NH2:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C@H:2]2[C@H:7]3[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]3[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:3]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86598915HCID 86598915, compound

Product 1

HCID 86598920HCID 86598920, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-tert-butyl 3-methyl (1R,3S,4R,6R)-6-amino-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 29-3 (321 mg) in pyridine (4 mL), was added p-toluenesulfonyl chloride (249 mg). The mixture was stirred at room temperature for 1 hr. The resulting mixture was evaporated in vacuo, and the residue chromatographed on silica gel eluting with hexane and ethyl acetate (1:1) to give the target compound (440 mg)

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue chromatographed on silica gel eluting with hexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-94258ef9ed9e4c478a1fe7b77d011681
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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