Lithium Hydroxide → HCID 59118222, compound

HRID 896871Notes

Reaction equation

HRID 896871 reaction equation
[OH:1][C@H:2]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:3][NH:4][CH2:5][C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[C:18]([O:20]C)=[O:19])[CH:12]=2)[O:7]1.[Li+].[OH-]>C1COCC1.CO.O>[OH:1][C@H:2]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:3][NH:4][CH2:5][C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[C:18]([OH:20])=[O:19])[CH:12]=2)[O:7]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59118229HCID 59118229, compound

Product 1

HCID 59118222HCID 59118222, compoundYield 70.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[(2R)-2-({[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino}-methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate (Example 83, 60 mg, 0.143 mmol) in THF (0.50 mL) and MeOH (0.50 mL) was added LiOH (1.0 mL of a 2.0 M aq solution), and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with 1.0 mL H2O and purified via preparative HPLC (gradient of 100:0 0.1% TFA/H2O:acetonitrile to 30:70 0.1% TFA/H2O:acetonitrile). The peak of interest was collected and concentrated in vacuo to provide 41 mg of desired final product as a bis-trifluoroacetic acid (TFA) salt; 1H NMR (DMSO-d6, δ): 1.68-1.80 (m, 1 H), 2.04-2.18 (m, 1 H), 2.72-2.90 (m, 2 H), 3.22-3.50 (m, 4 H), 4.58 (dd, 1 H), 5.41 (d, 1 H), 6.82 (d, 1 H), 7.02 (d, 1 H), 7.04 (s, 1 H), 7.30-7.40 (m, 2 H), 7.50 (t, 1 H), 7.62 (d, 1 H), 8.01 (t, 1 H), 8.58 (d, 1 H), 8.82 (d, 1 H), 8.90 (s, 1 H), 9.44 (bs, 1 H), 9.64 (bs, 1 H) MS: m/z=415.2 [M+H]+.

Workup

  1. custompurified via preparative HPLC (gradient of 100:0 0.1% TFA/H2O:acetonitrile to 30:70 0.1% TFA/H2O:acetonitrile)
  2. customThe peak of interest was collected
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e75529cc6fe3465bbd9db98859494f76
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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