Acetonitrile → Benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate

HRID 708474Notes

Reaction equation

HRID 708474 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][C@@H:17]2[C@H:20]([N:21]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:22](=[O:31])[O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19](=[O:41])[N:18]2CC2C=CC(OC)=CC=2OC)[N:13]=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC#N.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][C@@H:17]2[C@H:20]([N:21]([CH2:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)[C:22](=[O:31])[O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19](=[O:41])[NH:18]2)[N:13]=[N:12]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24412Potassium PersulfateHCID 62657Potassium Phosphate, TribasicHCID 118379592Benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate

Product 1

HCID 118379866Benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared in analogous manner to example 82 step 5, using benzyl ((2R,3S)-2-((1-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate (57.2 mg, 0.080 mmol), CH3CN (762 μl), water (381 μl), potassium peroxydisulfate (31 mg, 0.12 mmol), and potassium phosphate, dibasic (19 mg, 0.109 mmol). 20.2 mg. LCMS: Rt=0.89 min, m/z=565.3 (M+1). Method 2m_acidic.

Workup

  1. customPrepared in analogous manner to example 82 step 5

Sources & evidence

ORD record
ord-03c1bf20c4d2468b8ec4d6e8dec52f68
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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