Benzene, 2-azido-1,3-difluoro- → (2S,3S)-ethyl-3-((S)-1-((1-mesityl-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

HRID 1478647Notes

Reaction equation

HRID 1478647 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:24])[NH:10][C@@H:11]([CH2:18][C:19]2[N:20]=[CH:21][S:22][CH:23]=2)[C:12](=[O:17])[NH:13][CH2:14][C:15]#[CH:16])[O:7]1)=[O:5])[CH3:2].[N:25]([C:28]1C(F)=CC=[CH:30][C:29]=1F)=[N+:26]=[N-:27].CCCC[Sn](OC(C)=O)(CCCC)CCCC.[CH3:53][C:54](O)([CH3:56])[CH3:55].[CH3:58][CH2:59]O.O>[O-]S([O-])(=O)=O.[Cu+2]>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:24])[NH:10][C@@H:11]([CH2:18][C:19]2[N:20]=[CH:21][S:22][CH:23]=2)[C:12]([NH:13][CH2:14][C:15]2[N:27]=[N:26][N:25]([C:28]3[C:29]([CH3:30])=[CH:55][C:54]([CH3:56])=[CH:53][C:59]=3[CH3:58])[CH:16]=2)=[O:17])[O:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11579166Benzene, 2-azido-1,3-difluoro-HCID 16682741Tributyltin acetateHCID 71817782(2S,3S)-ethyl-3-((S)-1-oxo-1-(prop-2-ynylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylateHCID 86659795HCID 86659795, compound

Product 1

HCID 131736518(2S,3S)-ethyl-3-((S)-1-((1-mesityl-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylateYield 42.8%

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

The general click procedure was used substituting the following quantities using: 37 (48 mg, 0.14 mmol); 2-azido-1,3-difluorobenzene (24 mg, 0.15 mmol); CuSO4 (3.5 mg, 0.02 mmol); NaAsc (18 mg, 0.09 mmol); TBTA (12 mg, 0.01 mmol); in t-BuOH/EtOH/H2O (1:1:0.5); afforded 47 as a white solid (30 mg, 42.8%). 1H NMR (400 MHz, DMSO-d6): δ 8.79-8.74 (d, 1H, J=1.79 Hz); 7.68-7.64 (m, 2H); 7.50 (s, 1H): 7.36-7.34 (d, 2H); 7.28-7.26 (d, 2H), 7.15-7.10 (m, 2H), 6.98 (s, 1H); 5.50 (s, 1H); 4.83-4.78 (m, 1H); 4.59-4.58 (d, 1H); 4.29-4.25 (m, 2H); 3.99-3.97 (q, 1H); 3.81 (s, 3H); 3.69-3.68 (m, 3H); 3.55-3.54 (d, 1H); 3.37-3.19 (abq, 2H); 2.35 (s, 3H); 1.93 (s, 3H) 1.33-1.29 (t, 3H). 13C NMR (DMSO-d6, 100 MHz): 169.25, 165.62, 153.65, 152.98, 144.93, 140.11, 134.51, 134.50, 128.12, 124.69, 115.88, 63.51, 52.69, 52, 78, 51.98, 48.66, 34.54, 33.10, 20.69, 16.89, 13.52.

Sources & evidence

ORD record
ord-318969390eb547c8985a560829e377fe
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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