N-bromobutanimide → HCID 86701093, compound

HRID 1396232Notes

Reaction equation

HRID 1396232 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:17]([CH2:18][OH:19])[O:16][C@H:15]3[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]3)[C@H:10]2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:5][CH:4]=1.C1C(=O)N(Br)C(=O)C1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].ClCCl.O.CC1(C)N([O])C(C)(C)CCC1>[CH3:22][N:20]([CH3:21])[C:13]1[S:14][C@H:15]2[O:16][C@H:17]([CH:18]=[O:19])[C@@H:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=3)[C@H:10]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[C@H:11]2[N:12]=1

Participants

7

Reactant 2

HCID 67184N-bromobutanimideHCID 69083734HCID 69083734, compound

Product 1

HCID 86701093HCID 86701093, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 2724126TempoCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ((3aR,5R,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methanol (500 mg, 1.0 mmol), TBAB (16.5 mg, 0.05 mmol), KHCO3 (461 mg, 4.6 mmol) and TEMPO (8 mg, 0.05 mmol) in dichloromethane (25 mL) and H2O (5 mL) was added NBS (201 mg, 1.13 mmol) at 15° C. After stirred for 30 min, the reaction mixture was quenched by saturated Na2SO3 (5 mL). The organic layer was dried over anhydrous magnesium sulfate and condensed to provide a residue, which was purified by silica gel column, eluted with 20-30% ethyl acetate in dichloromethane to give compound 11 as a yellow syrup (320 mg, 75% pure). (ES, m/z): [M+H]+ 487.0. 1H NMR (300 MHz, CDCl3) δ 9.61 (s, 1H), 7.22-7.34 (m, 4H), 6.83-6.92 (m, 4H), 6.11-6.13 (d, J=6.0 Hz, 1H), 4.17-4.67 (m, 8H), 3.83 (s, 6H), 3.00-3.04 (s, 6H).

Workup

  1. customthe reaction mixture was quenched by saturated Na2SO3 (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and condensed
  3. customto provide a residue, which
  4. customwas purified by silica gel column
  5. washeluted with 20-30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-1a329fb0e9b64d12885c4343129cd2c5
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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