Allyl bromide → HCID 67271283, compound

HRID 601713Notes

Reaction equation

HRID 601713 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH2:13][N:12]([CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:11]([C@@H:28]([OH:40])[C@@H:29]([NH2:39])[CH2:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)[CH2:10]2)[CH:2]=[CH2:3].[C:41](=O)([O-])[O-:42].[K+].[K+].C(Br)C=C.C(OCC)(=O)C>CN(C=O)C>[F:38][C:33]1[CH:32]=[C:31]([CH:36]=[C:35]([F:37])[CH:34]=1)[CH2:30][C@H:29]1[C@@H:28]([C@H:11]2[CH2:10][C:9]3[C:14](=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH:6]=[CH:7][CH:8]=3)[CH2:13][N:12]2[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:40][C:41](=[O:42])[NH:39]1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59746638HCID 59746638, compound

Product 1

HCID 67271283HCID 67271283, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-benzhydryl-8-hydroxy-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step F (14), 40 mg, 0.076 mmol) in DMF (2 mL) were added potassium carbonate (52 mg, 0.38 mmol) and allyl bromide (73 mg, 0.61 mmol). The mixture was stirred at rt overnight. Ethyl acetate (100 mL) was added and the mixture was washed with H2O (70 mL) twice, and dried over Na2SO4, and concentrated under vacuum to give the title compound: 1H NMR (CDCl3, 500 MHz) δ 2.50 (1H, m), 2.76 (1H, d, J=15 Hz), 2.90 (1H, d, J=35 Hz), 3.19 (1H, m), 3.26 (1H, dd, J=5, 10 Hz), 3.75 (1H, d, J=20 Hz), 3.80 (1H, m), 4.00 (1H, m), 4.13 (1H, d, J=20 Hz), 4.40 (2H, m), 4.72 (1H, dd, J=5, 10 Hz), 4.83 (1H, s), 4.87 (1H, s), 5.12-5.17 (2H, m), 5.84 (1H, m), 6.65 (1H, d, J=10 Hz), 6.75-6.80 (4H, m), 7.13-7.16 (1H, m), 7.19-7.32 (6H, m), 7.36 (2H, d, J=5 Hz), 7.42 (2H, d, J=5 Hz). MS (ESI) (M+H)+ 567.19.

Workup

  1. washthe mixture was washed with H2O (70 mL) twice
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2749908971664f26b3a9be43bc88f83a
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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