Lithium Hydroxide → HCID 59746631, compound

HRID 601705Notes

Reaction equation

HRID 601705 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[O:9]C(=O)[NH:7]1.[Li+].[OH-]>CCO.O>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:12]2[C@@H:11]([C@@H:10]([OH:9])[C@@H:6]([NH2:7])[CH2:5][C:4]3[CH:31]=[C:32]([F:34])[CH:33]=[C:2]([F:1])[CH:3]=3)[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67272289HCID 67272289, compound

Product 1

HCID 59746631HCID 59746631, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step A (8), 420 mg, 0.9 mmol) in EtOH (20 mL) was added a solution of LiOH (217 mg, 9 mmol) in H2O (5 mL). This reaction mixture was brought to 60° C. and stirred overnight. The mixture was then concentrated in vacuo. Ethyl ether (100 mL) was added to the mixture and washed with 1N HCl (80 mL) twice. The aqueous phase was basified to pH 12 with 50% aqueous NaOH solution. This mixture was extracted with ethyl acetate (100 mL) twice. The combined organic layer was dried (Na2SO4), and concentrated in vacuo to give 345 mg of the title compound of Preparation A: 1H NMR (CDCl3, 500 MHz) δ 1.78 (2H, brd s), 2.44 (1H, dd, J=10, 15 Hz), 2.93 (1H, m), 3.01-3.07 (3H, m), 3.36 (1H, s), 3.60-3.69 (3H, m), 3.80 (3H, s), 6.69 (1H, m), 6.77-6.81 (2H, m), 6.86 (2H, d, J=10 Hz), 6.98 (1H, d, J=5 Hz), 7.12-7.18 (3H, m), 7.24 (2H, d, J=10 Hz). MS (ESI)(M+H)+ 439.12.

Workup

  1. customwas brought to 60° C.
  2. concentrationThe mixture was then concentrated in vacuo
  3. additionEthyl ether (100 mL) was added to the mixture
  4. washwashed with 1N HCl (80 mL) twice
  5. extractionThis mixture was extracted with ethyl acetate (100 mL) twice
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto give

Sources & evidence

ORD record
ord-9d3844cb672445ba97912cebfe6daf17
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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