N-bromobutanimide → (S)-tert-butyl 1-(N-(5-bromo-4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 2109728Notes

Reaction equation

HRID 2109728 reaction equation
[OH:1][C:2]([CH3:40])([CH3:39])[C:3]#[C:4][C:5]1[N:6]=[C:7]([N:10]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11][C@@H:12]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:8][CH:9]=1.C1C(=O)N([Br:48])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:48][C:9]1[S:8][C:7]([N:10]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11][C@@H:12]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[N:6][C:5]=1[C:4]#[C:3][C:2]([OH:1])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57634169(S)-tert-butyl 1-(N-(4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57634127(S)-tert-butyl 1-(N-(5-bromo-4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamateYield 24.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(S)-tert-butyl 1-(N-(4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.18 g, 0.31 mmol) was taken up in 5 mL of CCl4 and NBS (0.11 g, 0.62 mmol) was added. After 3 hours, the solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (5% to 40% EtOAc/hexanes) to afford (S)-tert-butyl 1-(N-(5-bromo-4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.05 g, 24% yield) as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (5% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c88b2964f0c54a1197e7479a7c5e9daa
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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