Nitrogen → HCID 131733501, compound

HRID 2280381Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of trans-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (J. Med. Chem. 2010, 53, 6730-6746) (320 mg, 1.40 mmol) in pyridine (3 mL) was added TsCl (588 mg, 3.00 mmol). The mixture was stirred at 5° C. overnight. The solvent was removed under reduced pressure and the mixture was partitioned between CH2Cl2 and 10% aq. NaHCO3. The organic layer was washed with water, dried over MgSO4, and the solvent removed under reduced pressure. The residue was purified by FC (Hept/EA, 9.5:0.5→8:2) to afford trans-tert-butyl 3-azido-4-(tosyloxy)pyrrolidine-1-carboxylate as a colorless oil. LC-MS-conditions 08: tR=0.96 min; [M-CH3+H]+=368.10. TLC: rf (Hept/EA, 8:2)=0.22.

Workup

customThe solvent was removed under reduced pressure
customthe mixture was partitioned between CH2Cl2 and 10% aq. NaHCO3
washThe organic layer was washed with water
dry with materialdried over MgSO4
customthe solvent removed under reduced pressure
customThe residue was purified by FC (Hept/EA, 9.5:0.5→8:2)

Sources & evidence

ORD record: ord-6828013b0693456380ee2040b3f08cc1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139524B2

Reaction notes

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